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Chelat‐kontrollierte diastereoselektive Addition an α,ß‐Epoxy‐Aldehyde
Author(s) -
Ipaktschi Junes,
Heydari Akbar,
Kalinowski HansOtto
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.19941270519
Subject(s) - chemistry , epoxy , aldehyde , trimethylsilyl cyanide , selectivity , stereoselectivity , chelation , trimethylsilyl , cyanide , organic chemistry , medicinal chemistry , catalysis
Chelate‐Controlled Diastereoselective Addition to α,β‐Epoxy Aldehydes LiClO 4 ‐mediated reaction of trans ‐substituted α,β‐epoxy aldehydes 1 with allyltributyltin ( 2 ) or trimethylsilyl cyanide provides a general method for the synthesis of the corresponding syn ‐alcohols 3 with high selectivity. In the case of cis ‐substituted α,β‐epoxy aldehydes the selectivity depends on the size of the substituents.