Enantioselective C−C Bond Formation by Rhodium-Catalyzed Tandem Ylide Formation/[2,3]-Sigmatropic Rearrangement between Donor/Acceptor Carbenoids and Allylic Alcohols

2010 ◽  
Vol 132 (1) ◽  
pp. 396-401 ◽  
Author(s):  
Zhanjie Li ◽  
Huw M. L. Davies
Keyword(s):  
Bond Formation ◽  
Sigmatropic Rearrangement ◽  
Allylic Alcohols ◽  
Donor Acceptor

Regioselective Carbon-Carbon Bond Formation in Titanium Mediated Reaction of Ethylmagnesium Bromide with Allylic Alcohols and Allylic Ethers

Synlett ◽  
2001 ◽  
Vol 2001 (01) ◽  
pp. 0049-0052 ◽  
Author(s):  
Oleg G. Kulinkovich ◽  
Oleg L. Epstein ◽  
Vladimir E. Isakov ◽  
Ekaterina A. Khmel'nitskaya
Keyword(s):  
Bond Formation ◽  
Allylic Alcohols ◽  
Ethylmagnesium Bromide ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Allylic Ethers

CpRu-catalyzed asymmetric dehydrative allylation

2013 ◽  
Vol 85 (6) ◽  
pp. 1121-1132 ◽  
Author(s):  
Masato Kitamura ◽  
Kengo Miyata ◽  
Tomoaki Seki ◽  
Namdev Vatmurge ◽  
Shinji Tanaka
Keyword(s):  
Heterocyclic Compounds ◽  
Bifunctional Catalyst ◽  
High Reactivity ◽  
Allylic Alcohols ◽  
Chiral Catalysts ◽  
Carbocyclic Compounds ◽  
Donor Acceptor ◽  
High Utility ◽  
Operational Simplicity

Asymmetric Tsuji–Trost allylation is one of the key chiral technologies for construction of pharmaceutically important compounds because of the high utility of alkenyl-substituted products. Particularly, the dehydrative system using allylic alcohols and protic nucleophiles has started to attract the attention of organic synthetic chemists from the viewpoints of atom and step economy, environmental benignity, and operational simplicity. In this paper, two types of new chiral CpRu catalysts, which have been developed on the basis of redox-mediated donor–acceptor bifunctional catalyst (RDACat) concept, are presented. Complementary use of the chiral catalysts has realized the syntheses of a wide rage of carbocyclic compounds, saturated N- or O-heterocyclic compounds with high reactivity, regioselectivity, enantioselectivity, productivity, and generality.

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