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

作者：Pouyan Haghshenas, J. Wilson Quail, Michel Gravel · 发表于：The Journal of Organic Chemistry · 年份：2016 · DOI：10.1021/acs.joc.6b02568 · 被引用次数：30 · 研究领域：N-Heterocyclic Carbenes in Organic and Inorganic Chemistry、Catalytic Cross-Coupling Reactions、Coordination Chemistry and Organometallics

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.