Investigating the π-facial discrimination phenomenon in the conjugate addition of amines to chiral crotonates: A convenient basis for the rational design of chiral auxiliaries

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2293-2304

  Dumas, Françoise ^a   Mezrhab, Brahim ^a   D'Angelo, Jean ^a   Riche, Claude ^a   Chiaroni, Angèle ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000778942     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951414r     Document Type: Article

References (40)

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19. We are indebted to Dr. Robert Azerad (CNRS, Université René Descartes, Paris) for these experiments.
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28. Thus, for example, in the condensation of thiophenol to isomeric amides 14, in the presence of catalytic amounts of LiSPh, the anti-addition adduct predominates from E-substrate, while the syn-addition product predominates from the Z-isomer; both processes proceeded with the same degree of stereoselectivity (90% de) (Chart 6): Miyata, O.; Shinada, T.; Ninomiya, I.; Naito, T. Tetrahedron Lett. 1991, 32, 3519-3522.
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