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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.