Synthesis of geminal dimetal-substituted terminal alkenes utilizing a cuprate rearrangement: Toward an efficient and general access to trisubstituted olefins

Preparation of 1,1-dimetalated-1-alkenes was realised via metalate rearrangements in the opening of lithiodihydrofuran 6 by reaction with dilithium stannyl-, silyl-, alkyl- and aryl(cyano)cuprates and quenching with electrophilic agents. Several hetero (E)-and (Z)-1,1-dimetalated alkene derivatives...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 16; pp. 2530 - 2534
Main Authors Le Menez, P, Brion, JD, Lensen, N, Chelain, E, Pancrazi, A, Ardisson, J
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 14.11.2003
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
metalate rearrangement
HYDROSTANNYLATION
C-10-C-15
trisubstituted olefins
STANNYL
(+/-)-DES-EPOXY-ROSARAMYCIN
STANNYLCUPRATION
lithium
TRANSMETALATION
EPOTHILONES
tin
STANNYLMETALLATION
copper
STEREOSELECTIVE-SYNTHESIS
DERIVATIVES
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Summary:Preparation of 1,1-dimetalated-1-alkenes was realised via metalate rearrangements in the opening of lithiodihydrofuran 6 by reaction with dilithium stannyl-, silyl-, alkyl- and aryl(cyano)cuprates and quenching with electrophilic agents. Several hetero (E)-and (Z)-1,1-dimetalated alkene derivatives were so produced in good to high yields and total stereocontrol.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2003-42445