与加纳醛发生的“醋酸酯型”羟醛缩合反应中的双重立体分化。多羟基化γ-氨基羰基化合物的立体控制合成。

Double stereodifferentiation in the "acetate-type" aldol reaction with garner's aldehyde. Stereocontrolled synthesis of polyhydroxylated gamma-amino carbonyl compounds.

作者信息

Vicario Jose L, Rodriguez Mónica, Badía Dolores, Carrillo Luisa, Reyes Efraim

机构信息

Departamento de Química Orgánica II, Facultad de Ciencias, Universidad del País Vasco-Euskal Herriko Unibertsitatea, P.O. Box E-644, 48080 Bilbao, Spain.

出版信息

Org Lett. 2004 Sep 2;6(18):3171-4. doi: 10.1021/ol0487433.

DOI:10.1021/ol0487433

PMID:15330615

Abstract

[reaction: see text] The aldol reaction of acetamide enolates with protected chiral alpha-amino-beta-hydroxy aldehyde 1 (Garner's aldehyde) has been performed in a stereocontrolled way under double stereodifferentiation conditions using pseudoephedrine as the additional chiral information source attached to the enolate reagent. In addition, the obtained adduct has been transformed into other valuable chiral building blocks such as gamma-amino-beta,delta-dihydroxy acids, esters, and ketones.

摘要

[反应：见正文] 以伪麻黄碱作为连接在烯醇盐试剂上的额外手性信息源，在双立体分化条件下，乙酰胺烯醇盐与受保护的手性α-氨基-β-羟基醛1（加纳醛）进行了立体控制的羟醛反应。此外，所得到的加合物已被转化为其他有价值的手性结构单元，如γ-氨基-β,δ-二羟基酸、酯和酮。