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Synthesis of New Alkenyl‐Substituted 2‐( tert ‐Butyldimethylsiloxy)‐cyclopropanecarboxylates and Their Diastereoselective Conversion into (Hydroxymethyl)cyclopropanes
Author(s) -
Hofmann Bernhard,
Reißig HansUlrich
Publication year - 1994
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.1491271133
Subject(s) - chemistry , hydroxymethyl , stereochemistry , enantioselective synthesis , organic chemistry , catalysis
Various new 2‐alkenyl‐substituted methyl 2‐( tert ‐butyldimethylsiloxy)cyclopropanecarboxylates 8‐14 were synthesized from siloxy dienes and methyl diazoacetate. Further substitution by deprotonation and reactions with electrophiles provided derivatives 15‐19 in good yields. Reduction of trans ‐configurated cyclopropanecarboxylates with LiAlH 4 afforded the corresponding trans ‐2‐( tert ‐butyldimethylsiloxy)‐1‐(hydroxymethyl)cyclopropanes in excellent yields. The related cis ‐compounds were not formed, but ring‐opened products derived thereof were isolated. This unexpected influence of the configuration of the starting material on the type of the product formed is discussed.