Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 36, Pages 14694-14697Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja306407x
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Funding
- National Natural Science Foundation of China [21172206, 20972147]
- National Basic Research Program of China [2010CB833300]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT1189]
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The NH2 group in primary allylic amines was substituted directly by sulfinate salts with excellent regio- and stereoselectivities. In the presence of 0.1 mol % [Pd(allyl)Cl](2), 0.4 mol % 1,4-bis(diphenylphosphino)butane (dppb), and excess boric acid, a range of alpha-unbranched primary allylic amines were smoothly substituted with sodium sulfinates in an alpha-selective fashion to give structurally diverse allylic sulfones in good to excellent yields with exclusive E selectivity. Replacing dppb with 1,1'-bi-2-naphthol (BINOL) allowed unsymmetric alpha-chiral primary allylic amines to be transformed into the corresponding allylic sulfones in good to excellent yields with excellent retention of ee. Importantly, the reaction complements known asymmetric methods in substrate scope via its unique ability to provide alpha-chiral allylic sulfones with high optical purity starting from unsymmetric allylic electrophiles.
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