Synthesis and synthetic utility of pyrrole carbinols: Versatile intermediates in organic synthesis

ORGN 54

Darren J. Dixon and Mark S. Scott. Department of Chemistry, University of Cambridge, Lensfield Rd, Cambridge, CB2 1EW, United Kingdom
Pyrrole carbinols, to our knowledge, represent the only acyclic amino carbinol which show significant and general stability. We herein describe their exploitation as a protecting group, their asymmetric synthesis and their utility in synthetic transformations.

Their chemoselective synthesis via the addition of lithium pyrrolate to a range of aldehydes is described; the base mediated regeneration of the aldehyde and; the exploitation of these basic conditions in tandem deprotection-HWE reaction sequences. The ability of this group to function as a protecting group is demonstrated for example by the synthesis of the Civet Cat methyl ester.

Studies towards their asymmetric synthesis by reduction of acyl pyrroles, together with ligand controlled addition to aldehydes and our investigations into the ability of this group to act as a stereodirecting group are described.

 

New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004