The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes by using chiral salen catalyst

Dianjun Chen, Li Guo, S. R.S.Saibabu Kotti, Guigen Li

Research output: Contribution to journalArticle

25 Scopus citations

Abstract

The first asymmetric catalytic halo aldol reaction of β-iodo allenoates with aldehydes was established. The reaction was successfully achieved by using (R,R)-SalenAlCl as the chiral catalyst and LiI as an additive at 0°C in dichloromethane. Moderate to good yields and up to 62% ee were obtained. The new system showed a good substrate scope in which both aromatic aldehydes and aliphatic aldehydes can be employed. The reaction provided the first catalytic and enantioselective approach to chiral β-iodo Baylis-Hillman ester adducts.

Original languageEnglish
Pages (from-to)1757-1762
Number of pages6
JournalTetrahedron Asymmetry
Volume16
Issue number10
DOIs
StatePublished - May 23 2005

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