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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.