Extremely efficient chiral induction in conjugate additions of p-tolyl α-lithio-β-(trimethylsilyl)ethyl sulfoxide and subsequent electrophilic trapping reactions

Journal of Organic Chemistry

Volumn 65, Issue 6, 2000, Pages 1758-1766

  Nakamura, Shuichi ^a   Watanabe, Yoshihiko ^a   Toru, Takeshi ^a  

^a NAGOYA INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; CARBOXYLIC ACID DERIVATIVE; ESTER DERIVATIVE; HALIDE; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONJUGATE; CONTROLLED STUDY; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034708719     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991635n     Document Type: Article

References (56)

1. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
2. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
3. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
4. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
5. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
6. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
7. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
8. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
9. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
10. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
11. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
12. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
13. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
14. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
15. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
16. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben- David, Y. Tetrahedron Lett. 1979, 4603.
17. For a recent review, see: (a) Walker, A. J. Tetrahedron: Asymmetry 1992, 3, 961. α-Sulfinyl carbanions derived from the following sulfoxides: Allyl sulfoxides: (b) Binns, M. R.; Chai, O. L.; Haynes, R. K.; Katsifis, A. A.; Schober, P. A.; Vonwiller, S. C. Tetrahedron Lett. 1985, 26, 1569. (c) Nokami, J.; Ono, T.; Wakabayashi, S.; Hazato, A.; Kurozumi, S. Tetrahedron Lett. 1985, 26, 1985. (d) Hua, D. H.; Venkataraman, S.; Coulter, M. J.; Sinai-Zingde, C. G. J. Org. Chem. 1987, 52, 719. (e) Hua, D. H.; Venkataraman, S.; Ostrander, R. A.; Sinai-Zingde, C. G.; MaCann, P. J.; Coulter, M. J.; Xu, M. R. J. Org. Chem. 1988, 53, 507. (f) Binns, M. R.; Haynes, R. K.; Katsifis, A. G.; Schober, P. A.; Vonwiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423. (g) Haynes, R. K.; Katsifis, A. G.; Vonwiller, S. C. J. Am. Chem. Soc. 1988, 110, 5411. (h) Swindell, C. S.; Blase, F. R.; Eggleston, D. S.; Krause, J. Tetrahedron Lett. 1990, 31, 5409. α-Sulfinyl ketimines: (i) Hua, D. H.; Bharathi, S. N.; Takusagawa, F.; Tsujimoto, A.; Panangadan, J. A. K.; Hung, M. H.; Brabo, A. A.; Erpelding, A. M. J. Org. Chem. 1989, 54, 5659. (j) Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998. (k) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144. Thioacetal monosulfoxides: (l) Hermann, J. L.; Richman, J. E.; Schlessinger, R. H. Tetrahedron Lett. 1973, 3271, 3275. (m) Ogura, K.; Yamashita, M.; Tsuchihashi, G. Tetrahedron Lett. 1978, 1303. (n) Colombo, L.; Gennari, C.; Resnati, G.; Scolastico, C. J. Chem. Soc., Perkin Trans. 1 1981, 1284. β-keto sulfoxides; (o) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178. (p) Matloubi, F. Solladie, G. Tetrahedron Lett. 1979, 2141. Other sulfoxide: (q) Ghera, E.; Ben-David, Y. Tetrahedron Lett. 1979, 4603.
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32. We reasonably assumed that the aldehyde approaches to the enolate from the endo direction of the bicyclic intermediate, shown in Figure 5, as in the reaction with alkyl halides. The trapping reactions of ester enolates with alkyl halides and aldehydes generally occur from the same direction; see the following. Alkylations: (a) Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1-64. (b) Frater, G. In Stereoselective Synthesis; Heimchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Houben-Weyl: New York, 1996; Vol. 2, pp 723- 791. Aldol reactions: (c) Braun, M. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Ed.; Houben-Weyl: New York, 1996; Vol. 3, pp 1612-1667.
33. We reasonably assumed that the aldehyde approaches to the enolate from the endo direction of the bicyclic intermediate, shown in Figure 5, as in the reaction with alkyl halides. The trapping reactions of ester enolates with alkyl halides and aldehydes generally occur from the same direction; see the following. Alkylations: (a) Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1-64. (b) Frater, G. In Stereoselective Synthesis; Heimchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Houben-Weyl: New York, 1996; Vol. 2, pp 723-791. Aldol reactions: (c) Braun, M. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Ed.; Houben-Weyl: New York, 1996; Vol. 3, pp 1612-1667.
34. We reasonably assumed that the aldehyde approaches to the enolate from the endo direction of the bicyclic intermediate, shown in Figure 5, as in the reaction with alkyl halides. The trapping reactions of ester enolates with alkyl halides and aldehydes generally occur from the same direction; see the following. Alkylations: (a) Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1-64. (b) Frater, G. In Stereoselective Synthesis; Heimchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Houben-Weyl: New York, 1996; Vol. 2, pp 723- 791. Aldol reactions: (c) Braun, M. In Stereoselective Synthesis; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Ed.; Houben-Weyl: New York, 1996; Vol. 3, pp 1612-1667.
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