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Enantioselective alkylative double ring-opening of epoxides derived from cyclic allylic ethers: synthesis of enantioenriched unsaturated diols.

Abstract:

A screen of external chiral ligands has led to enantioselective organolithium-induced alkylative double ring-opening of 3,4-epoxytetrahydrofuran 1 with n-BuLi to give 3-methyleneheptane-1,2-diol 3 in 75% yield and 55% ee in the presence of bisoxazoline 10, and in up to 60% ee in the presence of (-)-sparteine 2. Extending the alkylative double ring-opening reaction to epoxides derived from oxabicyclo[n.2.1]alkenes (n = 2.3) results in the formation of cycloalkenediols, which, when carried out ...

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Publication status:
Published

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Publisher copy:
10.1039/b212404a

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
Organic and biomolecular chemistry
Volume:
1
Issue:
7
Pages:
1139-1150
Publication date:
2003-04-05
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
URN:
uuid:dc8ee198-3302-4a6e-8599-a84908e90166
Source identifiers:
32435
Local pid:
pubs:32435
Language:
English

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