Introduction of C(5/6) side chains onto 2-azabicyclo[2.1.1]hexanes via a 6-anti-bromo-5-anti-hydroxy derivative-Reference-Cited by-同舟云学术

Introduction of C(5/6) side chains onto 2-azabicyclo[2.1.1]hexanes via a 6-anti-bromo-5-anti-hydroxy derivative

Published:2012-01 Issue:1 Volume:90 Page:121-130
ISSN:0008-4042
Container-title:Canadian Journal of Chemistry
language:en
Short-container-title:Can. J. Chem.

Author:

Krow Grant R.¹,Yu Fang¹,Sender Matthew¹,Gandla Deepa¹,Lin Guoliang¹,DeBrosse Charles¹,Ross Charles W.²

Affiliation:

1. Department of Chemistry, Temple University, Philadelphia, PA 19122, USA.

2. Department of Medicinal Chemistry, Merck Research Laboratories, Merck & Co., Inc., West Point, PA 19486-004, USA.

Abstract

Oxidation of the title bromoalcohol provided the strained ketone, 5-bromo-6-oxo-2-azabicyclo[2.1.1]hexane. Additions of nucleophiles to either this or the debrominated ketone have been used to introduce 5(6)-syn-alkyl and aryl groups, 5(6)-alkylidene linkages, and 5(6)-anti-alkyl and acyl substituents. Facial selectivity is for additions to the 6-bromo-5-ketone and 5-alkylidene azabicycles to occur from the face syn to the nitrogen atom. The bromine atom of the title alcohol has also been replaced by a 6-anti-(1-hydroxyethyl) substituent using a directed radical addition process. The stereoselective functionalization reactions expand the range of available methano-bridged pyrrolidines.

Publisher

Canadian Science Publishing

Subject

Organic Chemistry,General Chemistry,Catalysis

Link

http://www.nrcresearchpress.com/doi/pdf/10.1139/v11-112

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