Synthesis of chiral 3-substituted phthalides via rhodium(I)-catalyzed crossed alkyne cyclotrimerisation

Synlett

Volumn , Issue 11, 2002, Pages 1855-1859

  Witulski, Bernhard ^a   Zimmermann, Axel ^a  

^a University of Koblenz Landau   (Germany)

Author keywords

(S) 3 n butylphthalide; Alkyne cyclotrimerisation; Phthalides; Propargylic alcohols; Wilkinson's catalyst

Indexed keywords

ALCOHOL DERIVATIVE; ALKYNE; PHTHALIDE DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0036422193     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34883     Document Type: Article

References (76)

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31. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
32. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
33. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
34. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
35. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
36. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
37. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
38. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
39. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
40. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
41. Aryllithium reagents: (a) Takahashi, H.; Tsubuki, T.; Higashiyama, K. Chem. Pharm. Bull. 1991, 39, 3136. (b) Alexakis, A.; Sedrani, R.; Normant, J. F.; Mangeney, P. Tetrahedron: Asymmetry 1990, 1, 283. (c) Ogawa, Y.; Hosaka, K.; Chin, M.; Mitsuhashi, H. Heterocycles 1989, 29, 865. (d) Meyers, A. I.; Hanagan, M. A.; Trefonas, L. M.; Baker, R. J. Tetrahedron 1983, 39, 1991. (e) Asami, M.; Mukaiyama, T. Chem. Lett. 1980, 17. (f) Dialkyl- and arylzinc reagents: Ogawa, Y.; Saiga, A.; Mori, M.; Shibata, T.; Takagi, K. J. Org. Chem. 2000, 65, 1031. (g) See also: Nakano, H.; Kumagai, N.; Matsuzaki, H.; Kabuto, C.; Hongo, H. Tetrahedron: Asymmetry 1997, 8, 1391. (h) See further: Soai, K.; Hori, H.; Kawahara, M. Tetrahedron: Asymmetry 1991, 2, 253. (i) See also: Watanabe, M.; Hashimoto, N.; Araki, S.; Butsugan, Y. J. Org. Chem. 1992, 57, 742. (j) Organotitanium reagents: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Synthesis 1992, 681. (k) Another example: Olivero, A. G.; Weidmann, B.; Seebach, D. Helv. Chim. Acta 1981, 64, 2485. (l) Borane reagents: Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
42. BINAP-Ru(II) hydrogenation: (a) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (b) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (c) Transfer hydrogenation: Everaere, K.; Scheffler, J.-L.; Mortreux, A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (d) Nicatalyzed cross couplings: Lei, J.-G.; Hong, R.; Yuan, S.-G.; Lin. G.-Q. Synlett 2002, 927. (e) Bioreduction: Kitayama, T. Tetrahedron: Asymmetry 1997, 8, 253.
43. BINAP-Ru(II) hydrogenation: (a) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (b) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (c) Transfer hydrogenation: Everaere, K.; Scheffler, J.-L.; Mortreux, A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (d) Nicatalyzed cross couplings: Lei, J.-G.; Hong, R.; Yuan, S.-G.; Lin. G.-Q. Synlett 2002, 927. (e) Bioreduction: Kitayama, T. Tetrahedron: Asymmetry 1997, 8, 253.
44. BINAP-Ru(II) hydrogenation: (a) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (b) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (c) Transfer hydrogenation: Everaere, K.; Scheffler, J.-L.; Mortreux, A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (d) Nicatalyzed cross couplings: Lei, J.-G.; Hong, R.; Yuan, S.-G.; Lin. G.-Q. Synlett 2002, 927. (e) Bioreduction: Kitayama, T. Tetrahedron: Asymmetry 1997, 8, 253.
45. BINAP-Ru(II) hydrogenation: (a) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (b) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (c) Transfer hydrogenation: Everaere, K.; Scheffler, J.-L.; Mortreux, A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (d) Nicatalyzed cross couplings: Lei, J.-G.; Hong, R.; Yuan, S.-G.; Lin. G.-Q. Synlett 2002, 927. (e) Bioreduction: Kitayama, T. Tetrahedron: Asymmetry 1997, 8, 253.
46. BINAP-Ru(II) hydrogenation: (a) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. (b) Ohkuma, T.; Kitamura, M.; Noyori, R. Tetrahedron Lett. 1990, 31, 5509. (c) Transfer hydrogenation: Everaere, K.; Scheffler, J.-L.; Mortreux, A.; Carpentier, J.-F. Tetrahedron Lett. 2001, 42, 1899. (d) Nicatalyzed cross couplings: Lei, J.-G.; Hong, R.; Yuan, S.-G.; Lin. G.-Q. Synlett 2002, 927. (e) Bioreduction: Kitayama, T. Tetrahedron: Asymmetry 1997, 8, 253.
47. (a) Padwa, A.; Weingarten, M. D. J. Org. Chem. 2000, 65, 3722.
48. (b) Harland, P. A.; Hodge, P. Synthesis 1982, 223.
49. (c) Becher, J.; Nielsen, H. C.; Jacobsen, J. P.; Simonsen, O.; Clausen, H. J. Org. Chem. 1988, 53, 1862.
50. Sato, Y.; Ohashi, K.; Mori, M. Tetrahedron Lett. 1999, 40, 5231.
51. Bhatarah, P.; Smith, E. H. J. Chem. Soc., Perkin Trans. 1 1992, 2163.
52. Müller, E. Synthesis 1974, 761.
53. (a) Grigg, R.; Scott, R.; Stevenson, P. Tetrahedron Lett. 1982, 23, 2691.
54. (b) Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1357.
55. (c) Grigg, R.; Sridharan, V.; Wang, J.; Xu, J. Tetrahedron 2000, 56, 8967.
56. (a) Magnus, P.; Witty, D.; Stamford, A. Tetrahedron Lett. 1993, 34, 23.
57. (b) McDonald, F. E.; Zhu, H. Y. H.; Holmquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605.
58. (c) Witulski, B.; Stengel, T. Angew. Chem. Int. Ed. 1999, 38, 2426.
59. (d) Witulski, B.; Stengel, T.; Fernández-Hernández, J. M. Chem. Commun. 2000, 1965.
60. (e) Kotha, S.; Mohanraja, K. Chem. Commun. 2000, 1909.
61. (f) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745.
62. (g) Witulski, B.; Alayrac, C. Angew. Chem. Int. Ed. 2002, 41, 3281.
63. (a) Propargylic alcohol (S)-2h (94% ee) is commercially available. The product, (S)-2g was obtained with 88% ee after (S)-alpine borane reduction of the corresponding ketone as described in the literature: Overman, L. E.; Bell, K. L. J. Am. Chem. Soc. 1981, 103, 1851.
64. (b) For the synthesis of (+)-propargylic alcohols via addition of lithium acetylide to aldehydes, see: Midland, M. M. J. Org. Chem. 1975, 40, 2250.
65. For recent achievements in the synthesis of optical active propargylic alcohols, see: (a) Franz, D. E.; Tomooka, C. S.; Fässler, R.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373. (b) Schubert, T.; Hummel, W.; Müller, M. Angew. Chem. Int. Ed. 2002, 41, 634.
66. For recent achievements in the synthesis of optical active propargylic alcohols, see: (a) Franz, D. E.; Tomooka, C. S.; Fässler, R.; Carreira, E. M. Acc. Chem. Res. 2000, 33, 373. (b) Schubert, T.; Hummel, W.; Müller, M. Angew. Chem. Int. Ed. 2002, 41, 634.
67. (a) Birtwistle, D. H.; Brown, J. M.; Foxton, M. W. Tetrahedron 1988, 44, 7309.
68. (b) Maier, S.; Kazmaier, U. Eur. J. Org. Chem. 2000, 1241.
69. 2: C, 78.77; H. 5.09. Found: C, 78.82; H, 4.98
70. For reviews on the Mitsunobu reaction, see: (a) Dodge, J. A.; Nissen, J. S.; Presnell, M. Org. Synth. 1996, 73, 110. (b) Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127. (c) Hughes, D. L. Org. React. 1992, 42, 335. (d) Castro, B. R. Org. React. 1983, 29, 1. (e) Mitsunobu, O. Synthesis 1981, 1.
71. For reviews on the Mitsunobu reaction, see: (a) Dodge, J. A.; Nissen, J. S.; Presnell, M. Org. Synth. 1996, 73, 110. (b) Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127. (c) Hughes, D. L. Org. React. 1992, 42, 335. (d) Castro, B. R. Org. React. 1983, 29, 1. (e) Mitsunobu, O. Synthesis 1981, 1.
72. For reviews on the Mitsunobu reaction, see: (a) Dodge, J. A.; Nissen, J. S.; Presnell, M. Org. Synth. 1996, 73, 110. (b) Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127. (c) Hughes, D. L. Org. React. 1992, 42, 335. (d) Castro, B. R. Org. React. 1983, 29, 1. (e) Mitsunobu, O. Synthesis 1981, 1.
73. For reviews on the Mitsunobu reaction, see: (a) Dodge, J. A.; Nissen, J. S.; Presnell, M. Org. Synth. 1996, 73, 110. (b) Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127. (c) Hughes, D. L. Org. React. 1992, 42, 335. (d) Castro, B. R. Org. React. 1983, 29, 1. (e) Mitsunobu, O. Synthesis 1981, 1.
74. For reviews on the Mitsunobu reaction, see: (a) Dodge, J. A.; Nissen, J. S.; Presnell, M. Org. Synth. 1996, 73, 110. (b) Hughes, D. L. Org. Prep. Proced. Int. 1996, 28, 127. (c) Hughes, D. L. Org. React. 1992, 42, 335. (d) Castro, B. R. Org. React. 1983, 29, 1. (e) Mitsunobu, O. Synthesis 1981, 1.
75. The enantiopurity of the esters 3g-i was analyzed after their conversion to the phthalides 4f-h, that proceeded without any detectable racemisation.
76. +]