Download PDF
Synlett 2006(3): 0435-0439  
DOI: 10.1055/s-2006-926239
LETTER
© Georg Thieme Verlag Stuttgart · New York

The Baylis-Hillman Reaction with Chiral α-Amino Aldehydes under Racemization-Free Conditions

Fernando Coelho*a, Gaspar Diazb, Carlos A. M. Abellaa, Wanda P. Almeidac
a Laboratory of Synthesis of Natural Products and Drugs, DQO/IQ/Unicamp, PO Box 6154, 13084-971, Campinas, SP, Brazil
b Laboratory of Organic Synthesis and Natural Products, Unioeste, PO Box 520, 85900-970, Toledo, PR, Brazil
c Graduate Program in Cellular and Structural Biology, Institute of Biology/Unicamp, 13083-970, Campinas, SP, Brazil
Fax: +19(55)37883023; e-Mail: coelho@iqm.unicamp.br;
Further Information

Publication History

Received 26 October 2005
Publication Date:
06 February 2006 (online)

   Buy Article Permissions and Reprints All articles of this category
Zoom Image

Abstract

The Baylis-Hillman reaction with chiral α-amino aldehydes has been revisited. The reaction carried out under the influence of ultrasound avoids the aldehyde racemization almost completely, providing useful chiral substrates which can be used as starting materials for the synthesis of natural products. To demonstrate the synthetic applicability of these adducts, the easy preparation of a bicyclic lactam with an indolizidinic skeleton was accomplished.

Key words

aldehydes - amino aldehydes - alkaloids - ring closure - stereoselectivity