title: E- and Z-stereoselectivity in the preparation of enamides from glycidyl sulfonamides and carbamates.
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.
authors: Pharmaceutical Development, AstraZeneca R&D Charnwood, Bakewell Road, Loughborough, LE11 5RH, UK.
authors: Jack A
authors: JA
authors: Brown
authors: Vijay
authors: V
authors: Chudasama
authors: Melvyn E
authors: ME
authors: Giles
authors: Duncan M
authors: DM
authors: Gill
authors: Philip S
authors: PS
authors: Keegan
authors: William J
authors: WJ
authors: Kerr
authors: Rachel H
authors: RH
authors: Munday
authors: Karen
authors: K
authors: Griffin
authors: Andrew
authors: A
authors: Watts
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry*; D003520:Cyclophosphamide / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000577:Amides; D002219:Carbamates; C006188:sufosfamide; D003520:Cyclophosphamide