Memory of chirality in the enantioselective synthesis of β-lactams derived from amino acids. Influence of the reaction conditions

Synlett

Volumn , Issue 7, 2003, Pages 1007-1011

  Bonache, M Angeles ^a   Gerona Navarro, Guillermo ^a   Martín Martínez, Mercedes ^a   García López, M Teresa ^a   López, Pilar ^b   Cativiela, Carlos ^b   González Muñiz, Rosario ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b CSIC   (Spain)

Author keywords

Amino acids; AN solvent depedency; Enantioselectivity; Memory of chirality; lactams

Indexed keywords

1 METHYL 2 PYRROLIDINONE; 2 AZETIDINONE DERIVATIVE; ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; AMINO ACID DERIVATIVE; BASE; BETA LACTAM DERIVATIVE; ORGANIC COMPOUND; PHOSPHORANE DERIVATIVE; SOLVENT; TERT BUTYLAMINOTRIS(PYRROLIDINO)PHOSPHORANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CORRELATION ANALYSIS; CYCLIZATION; ENANTIOMER; ENANTIOSELECTIVITY; PARAMETER; REACTION ANALYSIS; SYNTHESIS;

EID: 0037561625     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-39301     Document Type: Article

References (37)

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6. For examples of memory of chirality through enolate intermediates see: (a) Kawabata, T.; Yahiro, K.; Fuji, K. J. Am. Chem. Soc. 1991, 113, 9694. (b) Kawabata, T.; Wirth, T.; Yahiro, K.; Suzuki, H.; Fuji, K. J. Am. Chem. Soc. 1994, 116, 10809. (c) Brewster, A. G.; Frampton, C. S.; Jayatissa, J.; Mitchell, M. B.; Stoodley, R. J.; Vohra, S. Chem. Cammun. 1998, 299. (d) Betts, M. J.; Pritchard, R. G.; Schofield, A.; Stoodley, R. J.; Vohra, S. J. Chem. Soc.,Perkin Trans. 1 1999, 1067. (e) Kawabata, T.; Suzuki, H.; Nagae, Y.; Fuji, K. Angew. Chem. Int. Ed. 2000, 39, 2155. (f) Kawabata, T.; Chen, J.; Suzuki, H.; Nagae, Y.; Kinoshita, T.; Chancharunee, S.; Fuji, K. Org. Lett. 2000, 2, 3883. (g) Brewster, A. G.; Jayatissa, J.; Mitchell, M. B.; Schofield, A.; Stoodley, R. J. Tetrahedron Lett. 2002, 43, 3919.
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25. + + 1).
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33. It has been described that the enantioselectivity of the alkylation of Phe derivatives can be controlled by regulating the aggregate structure of chiral enolate intermediates: (a) Kawabata, T.; Kawakami, S.; Fuji, K. Tetrahedron Lett. 2002, 43, 1465. (b) Kawabata, T.; Kawakami, S.; Shimada, S.; Fuji, K. Tetrahedron 2003, 59, 965.
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