135637-09-1Relevant articles and documents
Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters
Chen, Jingjia,Hu, Weipeng,Jin, Jing,Lovinger, Gabriel J.,Morken, James P.,Zhang, Chenlong
supporting information, p. 14189 - 14195 (2021/09/11)
In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.
Efficient Control of the Stereoselectivity in Reactions of 2-Oxy-Substituted Benzylic Radicals
Moufid, Nadira,Renaud, Philippe,Hassler, Carla,Giese, Bernd
, p. 1006 - 1012 (2007/10/02)
The stereoselectivity in reactions of 2-oxy-substituted radicals of type B was investigated.As expected, minimization of allylic 1,3-starin was the major controlling factor.Under standard conditions, only a modest level of stereoselectivity was observed.E
Weak Base Promoted β-Elimination Reactions in 1-Phenyl-1-propyl Derivatives. Evidence for an Intermediate in the E2C Reaction
Kwart, Harold,Wilk, Kazimiera A.
, p. 3038 - 3041 (2007/10/02)
We describe the observation of a nucleophile trigger mechanism in the case of the weak base promoted β-elimination (E2C process) and suggest permutational isomerism of TBP intermediates.Weak bases, namely, bromide and fluoride ions, bring about elimination in a bent transition state to which only a small fraction of a covalent bond to the nucleophile-base and some leaving group departure must be achieved in an orienting intermediate.These studies provide evidence for a TBP structure surrounding C-α in the 1-phenyl-1-propyl system and attribute the equal availability of abstractable H and D of both diastereoisomers to the action of the promoter bases.