Novel synthesis of chiral terminal allenes via palladium(0)-catalyzed reduction of mesylates of 2-bromoalk-2-en-1-ols bearing a protected amino group, using diethylzinc

A novel palladium(0)-catalyzed synthetic route to a series of chiral termin al allenes bearing an N-protected amino alkyl group has been developed. The palladium(0)-catalyzed reaction of mesylates of 2-bromoalk-2-en-1-ols bear ing an amino functionality, with diethylzinc affords the corresponding: ter minal allenes in good yields. Both (E)- and (Z)-bromomesylates can equally be used for the present reaction. yielding the desired allenes in comparabl e yields. (C) 2000 Elsevier Science Ltd. All rights reserved.