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Volumn 74, Issue 4, 2009, Pages 1627-1631

Diastereo- And enantioselective synthesis of β-Hydroxy-α-amino acids: Application to the synthesis of a key intermediate for lactacystin

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; CHIRAL AUXILIARIES; DIASTEREO SELECTIVITIES; ENANTIO-SELECTIVE SYNTHESIS; ENANTIOMERIC EXCESS; ENOLATES; FACILE SYNTHESIS; GOOD YIELDS; LACTACYSTIN; LITHIUM CHLORIDES; NUCLEOPHILIC ADDITIONS; RECOVERY YIELDS; STEREO-SELECTIVE;

EID: 64349109198     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8023973     Document Type: Article
Times cited : (28)

References (51)
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    • Willis, M. C.; Cutting, G. A.; Piccio, V. J.-D.; Durbin, M. J.; John, M. P. Angew. Chem. 2005, 117, 1567-1569; Angew. Chem., Int. Ed. 2005, 44, 1543-1545.
  • 10
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    • Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113-116. (b) Omura, S.; Matsuzaki, K; Fujimoto, T.; Kosuge, K.; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117-118.
    • (a) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113-116. (b) Omura, S.; Matsuzaki, K; Fujimoto, T.; Kosuge, K.; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117-118.
  • 12
    • 64349120080 scopus 로고    scopus 로고
    • Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. 1996, 108, 449-452; Angew. Chem., Int. Ed. 1996, 35, 451-454.
    • (b) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem. 1996, 108, 449-452; Angew. Chem., Int. Ed. 1996, 35, 451-454.
  • 17
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    • Makino, K.; Goto, T.; Hiroki, Y.; Hamada, Y. Angew. Chem. 2004, 116, 900-902; Angew. Chem. Int. Ed. 2004, 43, 882 -884.
    • (b) Makino, K.; Goto, T.; Hiroki, Y.; Hamada, Y. Angew. Chem. 2004, 116, 900-902; Angew. Chem. Int. Ed. 2004, 43, 882 -884.
  • 28
    • 48949114898 scopus 로고    scopus 로고
    • Wang, H.-F.; Ma, G.-H.; Yang, S.-B.; Han, R.-G.; Xu, P.-F. Tetrahedron: Asymmetry 2008, 19, 1630-1635. From (1R)-(+)-camphor, we can prepare both 1a and 1b (1:1.59) and only need four steps with 55% overall yield.
    • (g) Wang, H.-F.; Ma, G.-H.; Yang, S.-B.; Han, R.-G.; Xu, P.-F. Tetrahedron: Asymmetry 2008, 19, 1630-1635. From (1R)-(+)-camphor, we can prepare both 1a and 1b (1:1.59) and only need four steps with 55% overall yield.
  • 29
    • 0000409399 scopus 로고    scopus 로고
    • For references to early work on asymmetric synthesis of β-hydroxy-α-amino acids through glycine enolates, see: (a) Belokon, Y. N.; Bulychev, A. G.; Vitt, S. V.; Struchkov, Y. T.; Batsanov, A. S.; Timofeeva, T. V.; Tsyryapkin, V. A.; Ryzhov, M. G.; Lysova, L. A.; Bakhmutov, V. I.; Belikov, V. M. J. Am. Chem. Soc. 1985, 107, 4252-4259.
    • For references to early work on asymmetric synthesis of β-hydroxy-α-amino acids through glycine enolates, see: (a) Belokon, Y. N.; Bulychev, A. G.; Vitt, S. V.; Struchkov, Y. T.; Batsanov, A. S.; Timofeeva, T. V.; Tsyryapkin, V. A.; Ryzhov, M. G.; Lysova, L. A.; Bakhmutov, V. I.; Belikov, V. M. J. Am. Chem. Soc. 1985, 107, 4252-4259.
  • 32
    • 64349123981 scopus 로고    scopus 로고
    • The theoretical explanation for the high stereoselectivity of substitution reactions of 1a and 1b with alkyl halides has been made by quantum chemistry study; see ref 6d
    • The theoretical explanation for the high stereoselectivity of substitution reactions of 1a and 1b with alkyl halides has been made by quantum chemistry study; see ref 6d.
  • 33
    • 64349092202 scopus 로고    scopus 로고
    • The X-ray structure of aldol products CCDC Nos. 266588 (2c′), 266589 (3c′), 221192 (2d′), 221193 (2f), 266590 (3f), 266591 (3g), 221191 (2h), and 266592 (3i) contain the supplementary crystallographic data. These data can be obtained free of charge from www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K. Fax: (+44) 1223/336-033.
    • The X-ray structure of aldol products CCDC Nos. 266588 (2c′), 266589 (3c′), 221192 (2d′), 221193 (2f), 266590 (3f), 266591 (3g), 221191 (2h), and 266592 (3i) contain the supplementary crystallographic data. These data can be obtained free of charge from www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K. Fax: (+44) 1223/336-033.
  • 51
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    • Panek, J. S.; Masse, C. E. Angew. Chem. 1999, 111, 1161-1163; Angew. Chem. Int. Ed. 1999, 38, 1093-1095.
    • (e) Panek, J. S.; Masse, C. E. Angew. Chem. 1999, 111, 1161-1163; Angew. Chem. Int. Ed. 1999, 38, 1093-1095.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.