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

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 diastereo...

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Bibliographic Details
Published in:Journal of organic chemistry 2016-12, Vol.81 (24), p.12075-12083
Main Authors: Haghshenas, Pouyan, Quail, J. Wilson, Gravel, Michel
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.6b02568