Under solvent-free conditions the reaction of epoxides 1a–i with trimethylsilylazide (2) catalyzed by poly- stiryl-supported fluoride (PS-DABCOF2) has led to the efficient preparation of the corresponding O-TMS protected 1,2-azido alcohols 3a–i that, by treatment with Dowex-H, gave the related 1,2-azido alcohols 4a–i in excellent yields (83–99% and 82–96%, respectively). The use of a flow procedure has allowed us to significantly minimize waste in the preparation of representative 1,2-azido alcohols 4a, 4c and 4i that have been obtained with E-factors of 1.6, 2.1, and 1.9, respectively. The 1,2-amino alcohols 5a, 5c and 5f have been also prepared, in quantitative yields, by reduction of the corresponding O-TMS protected 1,2-azido alcohols 3a, 3c, and 3f by Pd on the Al3O3/HCOOH system.

A waste-minimized protocol for the preparation of 1,2-azido alcohols and 1,2-amino alcohols

CROTTI, PAOLO;
2013-01-01

Abstract

Under solvent-free conditions the reaction of epoxides 1a–i with trimethylsilylazide (2) catalyzed by poly- stiryl-supported fluoride (PS-DABCOF2) has led to the efficient preparation of the corresponding O-TMS protected 1,2-azido alcohols 3a–i that, by treatment with Dowex-H, gave the related 1,2-azido alcohols 4a–i in excellent yields (83–99% and 82–96%, respectively). The use of a flow procedure has allowed us to significantly minimize waste in the preparation of representative 1,2-azido alcohols 4a, 4c and 4i that have been obtained with E-factors of 1.6, 2.1, and 1.9, respectively. The 1,2-amino alcohols 5a, 5c and 5f have been also prepared, in quantitative yields, by reduction of the corresponding O-TMS protected 1,2-azido alcohols 3a, 3c, and 3f by Pd on the Al3O3/HCOOH system.
2013
Eleonora, Ballerini; Crotti, Paolo; Ileana, Frau; Daniela, Lanari; Ferdinando, Pizzo; Luigi, Vaccaro
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11568/233926
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