Scalable Synthesis of β-Amino Esters via Reformatsky Reaction with N-tert-Butanesulfinyl Imines

被引：22

作者：

Brinner, Kristin ^{[1
]}

Doughan, Brandon ^{[1
]}

Poon, Daniel J. ^{[1
]}

机构：

[1] Novartis Inst Biomed Res, Emeryville, CA 94608 USA

来源：

SYNLETT | 2009年 / 06期

关键词：

diastereoselectivity; stereoselective synthesis; chiral auxilaries; imines; amino acids; ASYMMETRIC-SYNTHESIS; ACID-DERIVATIVES; CONDENSATION;

D O I：

10.1055/s-0028-1087964

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

The Reformatsky reagents derived from ethyl bromoacetate and tert-butyl bromoacetate add cleanly, in high yield, and with good diastereoselectivity to N-tert-butanesulfinyl aldimines and ketimines. Importantly, this reaction scales well (>50 mmol), and affords products Upwards of 70% yield over three steps, starting from commercially available N-tert-butanesulfinamide, aldehydes, and ketones.

引用

页码：991 / 993

页数：3

共 16 条

[1]

Abele S, 2000, EUR J ORG CHEM, V2000, P1

[2]

Brinner K, 2005, ENANTIOSELECTIVE SYNTHESIS OF BETA-AMINO ACIDS, 2ND EDITION, P181, DOI 10.1002/0471698482.ch8

[3]

Pilot plant preparation of an αvβ3 integrin antagonist.: Part 1.: Process research and development of a (S)-β-amino acid ester intermediate:: Synthesis via a scalable, diastereoselective imino-reformatsky reaction [J].