Asymmetric Synthesis of α-Amino 1,3-Dithioketals from Sulfinimines (N-Sulfinyl Imines). Synthesis of (2S,3R)-(−)-3-Hydroxy-3-methylproline
- 14 August 2004
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (19), 3393-3395
- https://doi.org/10.1021/ol0485971
Abstract
[reaction: see text] N-Sulfinyl alpha-amino 1,3-dithioketals are prepared in high de and good yield by treating sulfinimines with lithio-1,3-dithianes. Selective removal of the N-sulfinyl or the thioketal groups affords stable alpha-amino 1,3-dithioketals and N-sulfinyl alpha-amino ketones, respectively. This new sulfinimine-derived chiral building block is employed in the asymmetric synthesis of polyoxypeptin amino acid (2S,3R)-(-)-3-hydroxy-3-methylproline.Keywords
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