SN2′-Regio- and Diastereoselective Allylation of Organozinc Reagents
- 1 February 1993
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 22 (2) , 357-360
- https://doi.org/10.1246/cl.1993.357
Abstract
Dialkylzinc reagents, R2Zn and R2Zn·LiCl, undergo an SN2′-regio- and diastereoselective allylation reaction with substituted allylic chlorides and phosphates in the presence of a coordinating additive.Keywords
This publication has 12 references indexed in Scilit:
- SN2' addition of cuprates to acyclic vinyloxiranes. Synthesis of tylactone and tylonolide subunitsThe Journal of Organic Chemistry, 1992
- Copper-catalyzed reactions of organotitanium reagents. Highly SN2'- and anti-selective and diastereo- and chemoselective alkylation of allylic chlorides and phosphatesThe Journal of Organic Chemistry, 1991
- Asymmetric carbon-carbon bond formation via sulfoxide-directed SN2' displacements of acyclic allylic mesylatesThe Journal of Organic Chemistry, 1991
- Mechanistic aspects of the formation of chiral allenes from propargylic ethers and organocopper reagentsJournal of the American Chemical Society, 1990
- Highly Selective Synthesis of (E)‐Alkene Isosteric Dipeptides With High Optical Purity via RCu(CN)Li·BF3 Mediated ReactionAngewandte Chemie International Edition in English, 1990
- Auxiliary-based, asymmetric SN2' reactions: a case of 1,7-relative stereogenesisThe Journal of Organic Chemistry, 1990
- Syntheses of isocarbacyclin by highly regioselective alkylation of allylic alcoholsTetrahedron, 1990
- Virtually complete diastereofacial selectivity in the SN2' allylation of organocopper reagentsJournal of the American Chemical Society, 1989
- Copper- and nickel-catalysis in SN2′-and SN2-regioselective allylation of organozinc reagentsTetrahedron Letters, 1988
- Stereoselective addition of organoccuprates to a chiral α-β ethylenic oxazolidine: mechanism, nature and reactivity of the intermediatesJournal of Organometallic Chemistry, 1983