Catalytic Asymmetric Conjugate Addition of Thiols to α,β-Unsaturated Thioamides: Expeditious Access to Enantioenriched 1,5-Benzothiazepines

被引:43
作者
Ogawa, Takanori [1 ]
Kumagai, Naoya [1 ]
Shibasaki, Masakatsu [1 ]
机构
[1] Inst Microbial Chem, Shinagawa Ku, Tokyo 1410021, Japan
关键词
1; 5-benzothiazepine; asymmetric catalysis; chemoselectivity; conjugate addition; synthetic methods; SULFA-MICHAEL ADDITION; N-ACYLATED OXAZOLIDIN-2-ONES; CHIRAL LEWIS-ACID; ENANTIOSELECTIVE PROTONATION; CARBONYL-COMPOUNDS; TERMINAL ALKYNES; TRANSFORMATIONS; CONSTRUCTION; ACTIVATION; THIOPHENOL;
D O I
10.1002/anie.201204365
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Softly does it: The title reaction proceeded under proton transfer conditions with a catalyst prepared from commercially available reagents to afford the desired product in high enantioselectivity. The reaction was compatible with a free amino group, thus allowing for expeditious access to enantiomerically enriched 1,5-benzothiazepines, which are important chemical entities in medicinal chemistry.
引用
收藏
页码:8551 / 8554
页数:4
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