Preparation and use of chloromethyl (−)??menthyl ether in the synthesis of optically pure α??branched α??amino nitriles

S Shatzmiller, BZ Dolithzky…

Index: Shatzmiller, Shimon; Dolithzky, Ben-Zion; Bahar, Eliezer Liebigs Annalen der Chemie, 1991 , # 4 p. 375 - 379

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Citation Number: 12

Abstract

Abstract The synthesis of optically pure chloromethyl (−)-menthyl ether (2b) and its use in the synthesis of di-(−)-menthyl acetal (−)-menthyl (+)-menthyl acetals are described. The diastereomeric mixed acetals 7a, b and 8a, b are easily obtainable from the nitrones 5 and 6, KCN and 2b. The mixtures of diastereomers are separated into the pure components 7a, 7b and 8a, 8b by simple silica gel column chromatography. Hydrolysis of these products ( ...