Asymmetry in the boronic acid Mannich reaction: diastereocontrolled addition to chiral iminium species derived from aldehydes and (S)-5-phenylmorpholin-2-one
- 1 January 1996
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 16,p. 1953-1954
- https://doi.org/10.1039/cc9960001953
Abstract
(S)-5-Phenylmorpholin-2-one† and a range of aliphatic aldehydes form chiral iminium intermediates which undergo diastereoselective Mannich reactions with 2-furylboronic acid. Single crystal X-ray analysis of methylated derivative 4 derived from major adduct 2g confirms the stereochemical course of the reaction.Keywords
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