title: Substrate-Controlled Diastereoselectivity Reversal in NHC-Catalyzed Cross-Benzoin Reactions Using N-Boc-N-Bn-Protected α-Amino Aldehydes.
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.
authors.affiliation: Department of Chemistry, University of Saskatchewan , 110 Science Place, Saskatoon, Saskatchewan S7N 5C9, Canada.
authors.forename: Pouyan
authors.initials: P
authors.lastname: Haghshenas
authors.affiliation: Department of Chemistry, University of Saskatchewan , 110 Science Place, Saskatoon, Saskatchewan S7N 5C9, Canada.
authors.forename: J Wilson
authors.initials: JW
authors.lastname: Quail
authors.affiliation: Department of Chemistry, University of Saskatchewan , 110 Science Place, Saskatoon, Saskatchewan S7N 5C9, Canada.
authors.forename: Michel
authors.identifier: 0000-0003-3656-7108
authors.initials: M
authors.lastname: Gravel