An acetone-derived chiral stabilised azomethine ylid: Synthesis of enantiomerically pure 5,5,-dimethylproline derivatives

Authors
Aldous, DJ Drew, MGB Hamelin, EMN Harwood, LM Jahans, AB Thurairatnam, S
Citation
Dj. Aldous et al., An acetone-derived chiral stabilised azomethine ylid: Synthesis of enantiomerically pure 5,5,-dimethylproline derivatives, SYNLETT, (12), 2001, pp. 1836-1840
Citations number
18
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
12
Year of publication
2001
Pages
1836 - 1840
Database
ISI
SICI code
0936-5214(200112):12<1836:AACSAY>2.0.ZU;2-V
Abstract
The chiral stabilised azomethine ylid 3 generated in situ via Lewis acid ca talysed condensation of(5S)-5-phenylmorpholin-2-one with 2.2-dimethoxypropa ne can be trapped diastereoselectively with singly and doubly activated dip olarophiles. The cycloadducts may be dismantled in one pot to furnish enant iomerically pure 5,5-dimethylproline derivatives.