1.
Chem Commun (Camb)
; 48(40): 4836-8, 2012 May 18.
Article
in English
| MEDLINE
| ID: mdl-22499212
ABSTRACT
A range of chiral, optically-enriched bicyclic oxabispidines were prepared from (S)-(-)-2,3-epoxypropylphthalimide using an efficient sequence featuring a stereocontrolled intramolecular Mannich reaction as the key transformation.
Subject(s)
Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/chemical synthesis , Crystallography, X-Ray , Cyclization , Molecular Conformation , Phthalimides/chemistry , Stereoisomerism
2.
E- and Z-stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates.
Org Biomol Chem
; 10(3): 509-11, 2012 Jan 21.
Article
in English
| MEDLINE
| ID: mdl-22124587
ABSTRACT
Treatment of glycidyl sulfonamides with LDA delivers the corresponding enesulfonamide with good selectivity for the E-isomer, whereas the corresponding carbamates exhibit selectivity for the Z-enecarbamate. An E1cB elimination mechanism proceeding from a substrate-base chelate complex is advanced as rationalisation of the latter set of Z-selective outcomes.
