Racemization in the Use of N-(9-(9-Phenylfluorenyl))Serine-Derived Cyclic Sulfamidates in the Synthesis of δ-Keto α-Amino Carboxylates and Prolines
- 1 August 2000
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 2 (17) , 2595-2598
- https://doi.org/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.Keywords
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