手性 BINOL-钛配合物催化的吲哚满酮与重氮乙酰胺的不对称 Darzens 反应。
Asymmetric Darzens Reaction of Isatins with Diazoacetamides Catalyzed by Chiral BINOL-Titanium Complex.
机构信息
Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences , 345 Ling Ling Road, Shanghai 200032, China.
Key Laboratory for Advanced Materials, Institute of Fine Chemicals, School of Chemistry & Molecular Engineering, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.
出版信息
J Org Chem. 2017 Dec 1;82(23):12647-12654. doi: 10.1021/acs.joc.7b02439. Epub 2017 Oct 31.
An efficient catalytic asymmetric Darzens reaction of N-protected isatins with diazoacetamides using a chiral BINOL/Ti(OPr) complex as the catalyst has been developed. This reaction is a straightforward method for the synthesis of spiro-epoxyoxindoles in 40-95% yields, up to >20:1 dr and up to >99% ee. A gram-scale reaction was also achieved in 95% yield with excellent stereoselectivity and enantioselectivity (>20:1 dr, >99% ee).
已开发出一种高效的手性 BINOL/Ti(OPr)配合物催化的 N-保护色胺与重氮乙酰胺的不对称 Darzens 反应。该反应是一种直接合成螺环氧吲哚的方法，产率为 40-95%，对映选择性高达>20:1，ee 值高达>99%。在克级规模反应中也获得了 95%的产率，具有极好的立体选择性和对映选择性（>20:1 dr，>99% ee）。
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