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Wuhan University Journal of Natural Sciences

, Volume 8, Issue 4, pp 1138–1142 | Cite as

Preparation of (R)- and (S)-2-Allyl-1, 3, 2-dinaphtho (α, β) [d.f] dioxaborepin and their reactions with aldehydes

  • Liu De-jun
  • Shan Zi-xing
  • Wang Guo-ping
  • Qin Jin-gui
Article

Abstract

(R)- and(S)-2-Allyl-1,3,2-dinaphtho (α,β) [d.f] dioxaborepin ((R)-2 and(S)-2) have been first prepared by the reaction of(R)-(+)- or(S)-(−)-1, 1′-bi-2-naphthol and triallylborane in THF at room temperature, respectively.(S)-2 and(R)-2 are sensitive to moisture and oxygen in air and disproportionate easily to triallylborane and 1,1′-bi-2 naphthyl bis (1,1′-bi-2-naphtholborate) at ambient temperature. However, THF is a stabilizer for them. The reactions of(R)-2 or(S)-2 and some aliphetic or aromatic aldehydes in CH2Cl2 at −78°C for several hours afforded β-alkylenyl alcohols in up to 84.8%ee. Among them, optically active 1-(3, 5-dichlorophenyl)-3-butenol and 1-(2-methoxyphenyl)-3-butenol were first prepared

Key words

1,1′-bi-2-naphthyl allylboronate preparation asymmetric allylation 

CLC number

O 621.3+O 621.3+91 

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Copyright information

© Springer 2003

Authors and Affiliations

  1. 1.College of Chemistry and Molecular SciencesWuhan UniversityWuhan, HubeiChina

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