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All‐carbon N‐heterocyclic Carbene‐catalyzed (3+2) Annulation using Donor‐Acceptor Cyclopropanes
Author(s) -
Candish Lisa,
Gillard Rachel M.,
Fernando Jared E. M.,
Levens Alison,
Lupton David W.
Publication year - 2016
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.201500102
Subject(s) - chemistry , annulation , carbene , catalysis , cyclopentanes , acceptor , medicinal chemistry , alkene , cyclopropanation , carbon fibers , organic chemistry , photochemistry , physics , condensed matter physics , materials science , composite number , composite material
Donor‐acceptor cyclopropanes are known to serve as dipole precursors capable of engaging in (3+2) annulations with electron‐deficient π‐systems. In 2013, the reaction of donor‐acceptor cyclopropanes with α,β‐unsaturated acyl fluorides in an all‐carbon (3+2) annulation was discovered. The reaction proceeds in good yields using the IMes NHC to provide diastereomerically pure β‐lactone‐fused cyclopentanes bearing four contiguous stereocentres. Subsequent studies demonstrated that N‐ t‐ butyl substituted homochiral morpholinone NHCs allowed the reaction to be achieved in up to 98 % ee . In this account, a background to this reaction is introduced, along with a complete account of the strengths, limitations and challenges encountered while developing this chemistry.