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One-pot process that efficiently generates single stereoisomers of 1,3-bisphosphinylpropanes having five chiral centers.

Authors
  • Zhang, He
  • Sun, Yong-Ming
  • Zhao, Yalei
  • Zhou, Zhong-Yang
  • Wang, Ji-Ping
  • Xin, Nana
  • Nie, Shao-Zhen
  • Zhao, Chang-Qiu
  • Han, Li-Biao
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Jan 02, 2015
Volume
17
Issue
1
Pages
142–145
Identifiers
DOI: 10.1021/ol503371r
PMID: 25521011
Source
Medline
License
Unknown

Abstract

P,C-stereogenic 1,3-bisphosphinylpropanes 3 that have up to five stereogenic centers could be obtained stereoselectively in high yields by a one-step reaction of (RP)-menthylphenylphosphine oxide 1 with α,β-unsaturated aldehydes 2 catalyzed by KOH at room temperature. A mechanism was proposed as to involve a stereoselective intermolecular 1,3'-phosphorus migration from the 1,2-adduct of 1 with 2 to another 2 generating a 1,4-adduct that subsequently reacts with 1 to produce 3.

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