Approach to synthesis of novel chiral 3-chloro-2(5H)- furanone and its application in asymmetric reactions

摘要

The synthetic method of the novel chiral synthon, 5-/-menthyloxy-3-chloro-2-(5H)- furanone 5a and its application in asymmetric reactions were investigated. 5a is easily obtained in highly optical purity, and acts as a stable acceptor of Michael addition with oxygen nucleophiles in tandem double Michael addition / internal nucleophilic substitution to offer the spiro-cyclopropane derivative containing four stereogenic centers 8, which it is difficult to obtain by routine methods.