SCOPUS 정보 검색 플랫폼

Volumn 7, Issue 5, 2005, Pages 799-802

Nonracemic homopropargylic alcohols via asymmetric allenylboration with the robust and versatile 10-TMS-9-borabicyclo[3.3.2]decanes

(2) Lai, Chunqiu a Soderquist, John A a

a UNIVERSITY OF PUERTO RICO (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE DERIVATIVE; BORANE DERIVATIVE; BROMINE DERIVATIVE; CRYSTALLIN; MAGNESIUM DERIVATIVE; PSEUDOEPHEDRINE;

ADDITION REACTION; AIR; ARTICLE; CHEMICAL REACTION; ENANTIOMER; GRIGNARD REACTION; PREDICTION; STEREOCHEMISTRY; SYNTHESIS;

ALCOHOLS; ALDEHYDES; ALKANES; BORANES; CATALYSIS; EPHEDRINE; INDICATORS AND REAGENTS;

EID: 15044354126 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol0476164 Document Type: Article

Times cited : (76)

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- (1970) Bull. Soc. Chim. Fr. , pp. 2171-2174
- Moreau, J.-L.¹ Gaudemar, M.²

18
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- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1970) Bull. Soc. Chim. Fr. , pp. 2175
- Moreau, J.-L.¹ Gaudemar, M.²

19
- 0000997935
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- (1982) Tetrahedron Lett. , vol.23 , pp. 719-722
- Corey, E.J.¹ Rucker, C.²

20
- 0010690719
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1983) J. Org. Chem. , vol.48 , pp. 5376-5377
- Wang, K.K.¹ Nikam, S.S.² Ho, C.D.³

21
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- (1999) J. Am. Chem. Soc. , vol.121 , pp. 9769-9780
- Reich, H.J.¹ Holladay, J.E.² Walker, T.G.³ Thompson, J.L.⁴

22
- 0000986355
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1984) Bull. Chem. Soc. Jpn. , vol.57 , pp. 2768
- Furata, K.¹ Ishiguro, M.² Haruta, R.³ Ikeda, N.⁴ Yamamoto, H.⁵

23
- 0000498840
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1982) Org. Chem. , vol.47 , pp. 2225-2227
- Ishiguro, M.¹ Ikeda, N.² Yamamoto, H.J.³

24
- 0028053497
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1994) Tetrahedron Lett. , vol.35 , pp. 8323-8324
- Keck, G.E.¹ Krishnamurthy, D.² Chen, X.³

25
- 0037530087
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (2003) Tetrahedron: Asymmetry , vol.14 , pp. 1603-1605
- Konishi, S.¹ Hanawa, H.² Maruoka, K.³

26
- 0000270567
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1981) Tetrahedron Lett. , vol.22 , pp. 1579-1582
- Daniels, R.G.¹ Paquette, L.A.²

27
- 0000253689
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1984) J. Org. Chem. , vol.49 , pp. 4565-4569
- Zweifel, G.¹ Hahn, G.²

28
- 0010646875
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1982) J. Org. Chem. , vol.47 , pp. 3364-3366
- Pearson, N.R.¹ Hahn, G.² Zweifel, G.³

29
- 0001137591
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1991) J. Org. Chem. , vol.56 , pp. 3211-3213
- Marshall, J.A.¹ Wang, X.-J.²

30
- 0000711640
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1990) J. Org. Chem. , vol.55 , pp. 6246-6248
- Marshall, J.A.¹ Wang, X.-J.²

31
- 0001652206
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1997) J. Org. Chem. , vol.62 , pp. 8976-8977
- Marshall, J.A.¹ Adams, M.D.²

32
- 0034832840
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 6199-6200
- Denmark, S.E.¹ Wynn, T.²

33
- 3142656623
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (2004) Org. Lett. , vol.6 , pp. 2137-2140
- Roy, S.¹ Banerjee, M.²

34
- 0032544714
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2392-2395
- Yu, C.-M.¹ Yoon, S.K.² Back, K.³ Lee, J.-Y.⁴

35
- 0000480560
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1980) J. Org. Chem. , vol.45 , pp. 3925-3927
- Danheiser, R.L.¹ Carini, D.J.²

36
- 0001728711
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1986) J. Org. Chem. , vol.51 , pp. 3870-3878
- Danheiser, R.L.¹ Carini, D.J.² Kwasigroch, C.A.³

37
- 0037073344
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (2002) Tetrahedron: Asymmetry , vol.13 , pp. 2449
- Nakajima, M.¹ Saito, M.² Hashimoto, S.³

38
- 76849098545
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 6392-6393
- Kobayashi, S.¹ Nishio, K.²

39
- 0005377429
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1974) J. Organomet. Chem. , vol.76 , pp. 297-304
- Farve, E.¹ Gaudemar, M.²

40
- 0010689701
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1974) J. Organomet. Chem. , vol.76 , pp. 305-313
- Farve, E.¹ Gaudemar, M.²

41
- 0001308870
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1995) J. Org. Chem. , vol.60 , pp. 8130-8131
- Brown, H.C.¹ Khire, U.R.² Narla, G.³

42
- 0010690719
- See, for Mg: (a) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2171-2174. (b) Moreau, J.-L.; Gaudemar, M. Bull. Soc. Chim. Fr. 1970, 2175. For Li: (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719-722. (d) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (e) Reich, H. J.; Holladay, J. E.; Walker, T. G.; Thompson, J. L J. Am. Chem. Soc. 1999, 121, 9769-9780. For Ti: (f) Furata, K.; Ishiguro, M.; Haruta, R.; Ikeda, N.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1984, 57, 2768. (g) Ishiguro, M.; Ikeda, N.; Yamamoto, H. J. Org. Chem. 1982, 47, 2225-2227. (h) Keck, G. E.; Krishnamurthy, D.; Chen, X. Tetrahedron Lett. 1994, 35, 8323-8324. (i) Konishi, S.; Hanawa, H.; Maruoka, K. Tetrahedron: Asymmetry 2003, 14, 1603-1605. For Zn, Al: (j) Daniels, R. G.; Paquette, L. A. Tetrahedron Lett. 1981, 22, 1579-1582. For Zn: (k) Zweifel, G.; Hahn, G. J. Org. Chem. 1984, 49, 4565-4569. (l) Pearson, N. R.; Hahn, G.; Zweifel, G. J. Org. Chem. 1982, 47, 3364-3366. For Sn: (m) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 3211-3213. (n) Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1990, 55, 6246-6248. (o) Marshall, J. A.; Adams, M. D. J. Org. Chem. 1997, 62, 8976-8977. (p) Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200. (q) Roy, S.; Banerjee, M. Org. Lett. 2004, 6, 2137-2140. (r) Yu, C.-M.; Yoon, S. K.; Back, K.; Lee, J.-Y. Angew. Chem., Int. Ed. 1998, 37, 2392-2395. For Si: (s) Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925-3927. (t) Danheiser, R. L.; Carini, D. J.; Kwasigroch, C. A. J. Org. Chem. 1986, 51, 3870-3878. (u) Nakajima, M.; Saito, M.; Hashimoto, S. Tetrahedron: Asymmetry 2002, 13, 2449. (v) Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392-6393. For B: (w) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 297-304. (x) Farve, E.; Gaudemar, M. J. Organomet. Chem. 1974, 76, 305-313. (y) Brown, H. C.; Khire, U. R.; Narla, G. J. Org. Chem. 1995, 60, 8130-8131. (z) Wang, K. K.; Nikam, S. S.; Ho, C. D. J. Org. Chem. 1983, 48, 5376-5377. (aa) Kulkarni, S. V.; Brown, H. C. Tetrahedron Lett. 1996, 37, 4125-4128. For In: (ab) Loh, T.-P.; Lin, M.-J.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 507-509.
- (1983) J. Org. Chem. , vol.48 , pp. 5376-5377
- Wang, K.K.¹ Nikam, S.S.² Ho, C.D.³

43
- 0029896271
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53
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54
- 15044355170
- note
- 11B NMR signal for 4 exhibits variability with the concentration of 4.

55
- 15044358872
- note
- 2, 25°C, 28 h).

56
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57
- 15044345567
- note
- Attempts to substitute other amino alcohols, such as 2-amino ethanol, for PE failed to produce a crystalline precipitate.

58
- 15044357647
- note
- The C-3 (propargylic) position in the (R)-Mosher chloride-derived esters of 6 is consistently shifted upfield (Δδ 0.1-0.3) when compared to those from the enantiomeric alcohols. Other NMR signals were also used (see Supporting Information).

59
- 15044364024
- note
- Performed using the Spartan 4.0.4a GL MM program.

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