Diastereoselective cycloalkylation of phosphoryl and thiophosphoryl acetonitriles by α,ψ‐dihalogenalkanes under phase transfer catalysis conditions

Abstract

Abstract Cycloalkylation of phosphoryl and thiophosphoryl acetonitriles 2 by α,ψ‐dihalogenalkanes was found to proceed diastereoselectively under phase transfer catalytic conditions yielding 1‐(phosphoryl)‐2‐methyl‐cycloalkane carbonitriles as trans‐isomers with identical configuration of asymmetric cyclic carbon atoms (R C * R C * ). In the case of additional asymmetric phosphorus atom in the starting substrate, trans‐isomers are formed as a mixture of diastereomers differing in the configuration of the phosphorus atom (S P * R C * R C * and R P * R C * R C * ). © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:13–21, 2006; Published online in Wiley InterScience ( www.interscience.wiley.com ). DOI 10.1002/hc.20186