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A room-temperature catalytic asymmetric synthesis of allenes with ECNU-Phos.

Authors
  • Wang, Yuli
  • Zhang, Wanli
  • Ma, Shengming
Type
Published Article
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Publication Date
Aug 07, 2013
Volume
135
Issue
31
Pages
11517–11520
Identifiers
DOI: 10.1021/ja406135t
PMID: 23869750
Source
Medline
License
Unknown

Abstract

Three-carbon axial chirality has been asymmetrically established from racemic one-carbon central chirality efficiently at room temperature: we report here the discovery of the first catalytic asymmetric carbonylation of readily available racemic propargylic carbonates to access optically active 2,3-allenoates with fairly high ee. The combination of [(π-allyl)PdCl]2 with [(R)-ECNU-Phos], a new chiral bisphosphine ligand based on a biphenyl skeleton, demonstrates high enantioselectivity. Both enantiomers of allenoates can be obtained at room temperature by applying either (R)- or (S)-ECNU-Phos.

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