Tetrahedron Letters p. 1265 - 1268 (1993)
Update date:2022-07-30
Topics: Synthesis Stereoselective Hydroboration Experimental
Brown, Herbert C.
Salunkhe, Ashok M.
A highly stereoselective synthesis of trans-cycloalkanopiperidines and cycloalkanopyrrolidines has been achieved via hydroboration of bromocycloalkenes with dichloroboranes.The intermediate bromocycloalkylboronic acids were converted into azidocycloalkylboronates.Addition of two equivalents of boron trichloride in dichloromethane generated dichloroboranes which, by an intramolecular cyclisation gave intermediates 11.These can be readily hydrolyzed to get the corresponding important nitrogen heterocycles in good yields and excellent stereochemical purities.
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