Racemization in the use of N-(9-(9-phenylfluorenyl))serine-derived cyclic sulfamidates in the synthesis of delta-keto alpha-amino carboxylates and prolines

L Wei; W D Lubell

doi:10.1021/ol006102b

Racemization in the use of N-(9-(9-phenylfluorenyl))serine-derived cyclic sulfamidates in the synthesis of delta-keto alpha-amino carboxylates and prolines

Org Lett. 2000 Aug 24;2(17):2595-8. doi: 10.1021/ol006102b.

Authors

L Wei¹, W D Lubell

Affiliation

¹ Département de chimie, Université de Montréal, Québec, Canada.

PMID: 10990405
DOI: 10.1021/ol006102b

Abstract

[reaction: see text]Ring opening of enantiopure N-(9-(9-phenylfluorenyl)serine-derived cyclic sulfamidates with beta-keto esters, beta-keto ketones, and dimethyl malonate gave a variety of gamma-substituted amino acid analogues in racemic form. Investigation of the mechanism for racemization revealed that beta-elimination occurred to form a dehydroalanine intermediate that underwent subsequent Michael addition.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Carboxylic Acids / chemical synthesis*
Cyclic S-Oxides / chemistry*
Oxazoles / chemistry*
Proline / analogs & derivatives*
Proline / chemical synthesis*
Stereoisomerism
Sulfonamides / chemistry*

Substances

Carboxylic Acids
Cyclic S-Oxides
Oxazoles
Sulfonamides
Proline