3 years ago

Asymmetric Darzens Reaction of Isatins with Diazoacetamides Catalyzed by Chiral BINOL–Titanium Complex

Asymmetric Darzens Reaction of Isatins with Diazoacetamides Catalyzed by Chiral BINOL–Titanium Complex
Jian-Wei Han, Guo-Li Chai, Henry N. C. Wong
An efficient catalytic asymmetric Darzens reaction of N-protected isatins with diazoacetamides using a chiral BINOL/Ti(OiPr)4 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).

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02439

DOI: 10.1021/acs.joc.7b02439

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