Substrate-Controlled Diastereoselectivity Reversal in NHC-Catalyzed Cross-Benzoin Reactions Using N-Boc-N-Bn-Protected α-Amino Aldehydes

  • J Org Chem. 2016 Dec 16;81(24):12075-12083. doi: 10.1021/acs.joc.6b02568.
Pouyan Haghshenas  1 ,  J Wilson Quail  1 ,  Michel Gravel  1
Affiliations
  • 1. Department of Chemistry, University of Saskatchewan , 110 Science Place, Saskatoon, Saskatchewan S7N 5C9, Canada.
PMID: 27978724 DOI: 10.1021/acs.joc.6b02568
Abstract

The effectiveness of utilizing N-Bn-N-Boc-α-amino aldehydes in cross-benzoin reactions with heteroaromatic aldehydes is demonstrated. The reaction is both chemoselective and syn-selective, making it complementary to the anti-selective cross-benzoin reaction of NHBoc-α-amino aldehydes. Good diastereoselectivity is obtained for a variety of amino aldehydes, including nonhindered ones. A Felkin-Anh model can be used to rationalize the observed diastereoselectivity.

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