Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/28024
Title: Partially hydrogenated 1,1 '-binaphthyl as ligand scaffold in metal-catalyzed asymmetric synthesis
Authors: Au Yeung, TTL
Chan, SS
Chan, ASC
Keywords: Alkylation
Alkynylation
Allylic alkylation
Asymmetric catalysis
Binaphthyl
Borane reduction
Conjugate addition
Ene-type cyclization
Epoxidation
Epoxide ring-opening
Hetero-Diels-Alder reaction
Hydroformylation
Hydrogenation
Octahydrobinaphthyl
Ring-closing metathesis
Trimethylsilylcyanation
Issue Date: 2003
Publisher: Wiley-V C H Verlag Gmbh
Source: Advanced synthesis & catalysis, 2003, v. 345, no. 5, p. 537-555 How to cite?
Journal: Advanced Synthesis & Catalysis 
Abstract: Although chiral binaphthyl-type ligands are already known to be effective over a broad spectrum of reactions, they sometimes fail in providing high enantioselectivities in some catalytic asymmetric reactions. This article summarizes recent attempts to elevate their performance by partly hydrogenating the naphthyl components of the binaphthyl. The synthetic routes to some of these ligands are briefly outlined. Positive results are observed in asymmetric hydrogenation, alkylation, borane reduction, epoxidation and hetero-Diels-Alder reactions. The function of the partially reduced binaphthyl skeleton, however, can sometimes be disadvantageous or ambiguous as illustrated in reactions such as asymmetric ring-closing metathesis, 1,4-conjugate addition, epoxidation, allylic alkylation, trimethylsilylcyanation, epoxide ring-opening and hydroformylation.
URI: http://hdl.handle.net/10397/28024
ISSN: 1615-4150
DOI: 10.1002/adsc.200202192
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