Asymmetric induction in the Baylis-Hillman reaction
1991; Elsevier BV; Volume: 2; Issue: 10 Linguagem: Inglês
10.1016/s0957-4166(00)86138-8
ISSN1362-511X
AutoresAndrew Gilbert, Trevor W. Heritage, Neil S. Isaacs,
Tópico(s)Chemical Synthesis and Analysis
ResumoAsymmetric induction in the product of the Baylis-Hillman reaction between an aldehyde and an acrylic compound in the presence of a tertiary amine base, may be controlled by chirality in the aldehyde, acrylic ester, base or solvent; R-CHO + CH2=CH-COOR' (B:, solvent) →CH2=C(C∗HROH)-COOR' Examples of each are described but the best stereochemical result, 100% ee, is obtained from the high pressure reaction of benzaldehyde with (-)-menthyl acrylate.
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