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Diastereoselective Synthesis of trans ‐1,2‐Dialkylcyclopropanols by the Kulinkovich Hydroxycyclopropanation of Homoallylic Alcohols
Author(s) -
Quan Long Guo,
Kim SeHo,
Lee Jae Chol,
Cha Jin Kun
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020617)41:12<2160::aid-anie2160>3.0.co;2-y
Subject(s) - enantiopure drug , cyclopropanation , stereoselectivity , work (physics) , bicyclic molecule , foundation (evidence) , scheme (mathematics) , titanium , chemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , mathematics , physics , political science , law , mathematical analysis , thermodynamics
The hydroxy group regulates the stereoselectivity in a modification of the titanium‐mediated Kulinkovich cyclopropanation procedure (see scheme). This method provides a diastereoselective synthesis of trans ‐1,2‐dialkylcyclopropanols, which starts with homoallylic alcohols and proceeds via a bicyclic titanacyclopropane intermediate. Enantiopure products may also be obtained if the corresponding chiral alcohols are used.