期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 57, 期 21, 页码 6251-6255出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201802963
关键词
asymmetric catalysis; atropisomerism; cross-coupling; cyclodehydration; peptides
资金
- National Institute of General Medical Sciences of the United States National Institutes of Health [GM-068649]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R37GM068649, R01GM068649] Funding Source: NIH RePORTER
Catalyst control over reactions that produce multiple stereoisomers is a challenge in synthesis. Control over reactions that involve stereogenic elements remote from one another is particularly uncommon. Additionally, catalytic reactions that address both stereogenic carbon centers and an element of axial chirality are also rare. Reported herein is a catalytic approach to each stereoisomer of a scaffold containing a stereogenic center remote from an axis of chirality. Newly developed peptidyl copper complexes catalyze an unprecedented remote desymmetrization involving enantioselective C-N bond-forming cross-coupling. Then, chiral phosphoric acid catalysts set an axis of chirality through an unprecedented atroposelective cyclodehydration to form a heterocycle with high diastereoselectivity. The application of chiral copper complexes and phosphoric acids provides access to each stereoisomer of a framework with two different elements of stereogenicity.
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