Enantioselective 5‐ endo ‐dig Carbocyclization of β‐Ketoesters with Internal Alkynes Employing a Four‐Component Catalyst System | Zendy

Suzuki Satoru | Zendy; Tokunaga Etsuko | Zendy; Reddy Dhande Sudhakar | Zendy; Matsumoto Takashi | Zendy; Shiro Motoo | Zendy; Shibata Norio | Zendy

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Enantioselective 5‐ endo ‐dig Carbocyclization of β‐Ketoesters with Internal Alkynes Employing a Four‐Component Catalyst System

Author(s) -

Suzuki Satoru,

Tokunaga Etsuko,

Reddy Dhande Sudhakar,

Matsumoto Takashi,

Shiro Motoo,

Shibata Norio

Publication year - 2012

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.201201060

Subject(s) - catalysis , enantioselective synthesis , yield (engineering) , allylic rearrangement , component (thermodynamics) , selectfluor , oxazoline , dig , chemistry , combinatorial chemistry , allylic alcohol , organic chemistry , medicinal chemistry , materials science , computer science , physics , metallurgy , thermodynamics , computer security

It takes four : The title reaction was achieved for the first time by employing a four‐component catalyst system, Zn II /Box‐Ph/Yb(OTf) 3 /HFIP, to deliver the products in high yields and enantioselectivities. Fluorination of one of the products with Selectfluor provides a medicinally attractive allylic fluoride in good yield. Box‐Ph=2,2′‐isopropylidine bis(4‐phenyl‐2‐oxazoline), HFIP=hexafluoroisopropyl alcohol.

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