Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/33040
Title: Enantioselective Hydroalkynylation of Non-Polar Carbon-Carbon Double Bonds: Iridium-Catalyzed Asymmetric Addition Reaction of Terminal Alkyne CH Bonds to Substituted Norbornadienes
Authors: Yang, Q
Choy, PY
Fan, B
Kwong, FY 
Keywords: Alkynes
Asymmetric catalysis
CH bonds
Iridium
Synthetic methods
Issue Date: 2015
Publisher: Wiley-VCH
Source: Advanced synthesis & catalysis, 2015, v. 357, no. 10, p. 2345-2350 How to cite?
Journal: Advanced synthesis & catalysis 
Abstract: This update describes the enantioselective addition of the terminal alkynyl CH bond across a non-polar CC double bond. Sterically congested substrates are often challenging in this type of reaction as these alkenyl substrates exhibit poor substrate-metal center coordination, and thus poor stereo-induction would result. The successful enantioselective hydroalkynylation of this type of system has sporadically been reported. We herein describe our progress for the example of vinyl-substituted norbornadiene derivatives. With the aid of an iridium complex in combination with the chiral SYNPHOS ligand, the addition products could be obtained smoothly with excellent enantioselectivities (up to 99% ee). In particular, the first examples of an acetylenic CH bond adding across azanorbornadienes are also disclosed.
URI: http://hdl.handle.net/10397/33040
ISSN: 1615-4150
EISSN: 1615-4169
DOI: 10.1002/adsc.201500465
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