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- Title
Stereogenic Phosphorus-Induced Diastereoselective Formation of Chiral Carbon during Nucleophilic Addition of Chiral HP Species to Aldehydes or Ketones.
- Authors
Zhang, He; Sun, Yong ‐ Ming; Yao, Lan; Ji, Si ‐ Yu; Zhao, Chang ‐ Qiu; Han, Li ‐ Biao
- Abstract
P,C-Stereogenic α-hydroxyl phosphinates or phosphine oxides were prepared from the additions of ( RP)-phosphinate to ketones or ( RP)-phosphine oxide to aldehydes, respectively, catalyzed by bases at room temperature in up to >99:1 diasteromeric ratio (d.r.P/d.r.C) and 99 % yields. The diastereoselectivity was induced by reversible equilibrium and different stabilities between two diastereomers of adduct, which was caused by the spatial interaction between menthoxyl or menthyl to alkyl groups of aldehydes or ketones.
- Subjects
NUCLEOPHILIC addition (Chemistry); ALDEHYDES; PHOSPHINE oxides; DIASTEREOISOMERS; ASYMMETRIC synthesis
- Publication
Chemistry - An Asian Journal, 2014, Vol 9, Issue 5, p1329
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201301650