期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 60, 期 51, 页码 26616-26621出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202112860
关键词
asymmetric hydrophosphination; chiral phosphine; C-P bond construction; N-heterocyclic carbene
资金
- Singapore National Research Foundation under its NRF Investigatorship [NRF-NRFI2016-06]
- Competitive Research Program [NRF-CRP22-2019-0002]
- Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award [RG7/20, RG5/19]
- Ministry of Education, Singapore, under its MOE AcRF Tier 2 [MOE2019-T2-2-117]
- Ministry of Education, Singapore, under its MOE AcRF Tier 3 Award [MOE2018-T3-1-003]
- Nanyang Research Award Grant
- Chair Professorship Grant
- Nanyang Technological University
- National Natural Science Foundation of China [21772029, 22071036, 21801051, 21961006]
- Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [(2020)004]
- 10 Talent Plan (Shicengci) of Guizhou Province [[2016]5649]
- Science and Technology Department of Guizhou Province [[2018]2802, [2019]1020)]
- Program of Introducing Talents of Discipline to Universities of China (111 Program) at Guizhou University [D20023]
- Guizhou University of Traditional Chinese Medicine
- Guizhou University
This study presents a novel carbene-catalyzed reaction for the efficient synthesis of chiral phosphines. These phosphines can serve as chiral ligands or catalysts with broad applications in asymmetric catalysis.
Disclosed herein is the first carbene-organocatalyzed asymmetric addition of phosphine nucleophiles to the in situ generated alpha,beta-unsaturated acyl azolium intermediates. Our reaction enantioselectively constructs carbon-phosphine bonds and prepares chiral phosphines with high optical purities. The phosphine products are suitable for transforming to chiral ligands or catalysts with applications in asymmetric catalysis. The diarylalkyl or trialkyl phosphine products from our catalytic reactions, air-sensitive and reactive in nature, can be trapped (and stored) in their sulfur-oxidized form for operational simplicities.
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