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Preparation of ( Z )‐Alk‐2‐ene‐1,5‐diols by the Titanocene(II)‐Promoted Cyclization of Thioacetals Possessing a Terminal Carbon−Carbon Double Bond
Author(s) -
Fujiwara Tooru,
Yanai Kenjirou,
Shimane Keiko,
Takamori Mayumi,
Takeda Takeshi
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200101)2001:1<155::aid-ejoc155>3.0.co;2-#
Subject(s) - chemistry , silylation , carbene , metathesis , double bond , stereoselectivity , medicinal chemistry , ring closing metathesis , carbon fibers , bond cleavage , titanium , carbon–carbon bond , stereochemistry , organic chemistry , catalysis , polymerization , materials science , composite material , composite number , polymer
Titanocene(II)‐promoted ring‐closing metathesis of the titanium carbene complexes prepared from [2,2‐bis(phenylthio)ethyl](but‐3‐enyloxy)dimethylsilanes or dimethyl(prop‐2‐enyl)silyl ethers of 3,3‐bis(phenythio)propanols gave seven‐membered cyclic unsaturated silyl ethers. Oxidative cleavage of a silicon−carbon bond of the cyclic silyl ethers resulted in olefinic diols, with high Z stereoselectivity.