Bis-Sulfamyl Imines: Potent Substrates for Asymmetric Additions of Arylboroxines under Rhodium Catalysis

被引:26
|
作者
Crampton, Rosemary [1 ]
Woodward, Simon [1 ]
Fox, Martin [2 ]
机构
[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England
[2] Chirotech Technol Ltd, Cambridge CB4 0GH, England
基金
英国工程与自然科学研究理事会;
关键词
asymmetric catalysis; boron; diarylmethylamines; protecting groups; rhodium; N-TOSYLARYLIMINES; ARYLATION; AMINES; LIGAND; REAGENTS; ACIDS; MILD;
D O I
10.1002/adsc.201000838
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Bis-sulfamyl imines are shown to be potentially ideal substrates for rhodium-catalysed asymmetric additions of arylboron nucleophiles as they show: (i) near perfect enantioselectivities (11 examples, 98-99+% ee), (ii) good to excellent diastereoselectivities (10-32:1 rac:meso), and (iii) high functional group tolerance in removal of the low molecular weight protecting group via mild heating in aqueous pyridine.
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页码:903 / 906
页数:4
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