scholarly journals A New Synthesis of 2-Sulfanyl Allylic Alcohols and α-Sulfanyl Ketones from Carbonyl Compounds and 1-Chloroalkyl p-Tolyl Sulfoxides with Carbon–Carbon Bond-Formation

2006 ◽  
Vol 54 (12) ◽  
pp. 1734-1738 ◽  
Author(s):  
Tsuyoshi Satoh ◽  
Yoshinori Takahashi ◽  
Yuuichi Shirai ◽  
Yukie Yamada
Keyword(s):  
Carbonyl Compounds ◽  
Bond Formation ◽  
Allylic Alcohols ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
New Synthesis

scholarly journals Transition Metal-Catalyzed α-Position Carbon–Carbon Bond Formations of Carbonyl Derivatives

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 861 ◽  
Author(s):  
Ha-Eun Lee ◽  
Dopil Kim ◽  
Ahrom You ◽  
Myung Hwan Park ◽  
Min Kim ◽  
...  
Keyword(s):  
Transition Metal ◽  
Carbonyl Compounds ◽  
Bond Formation ◽  
Chiral Ligand ◽  
Catalytic Systems ◽  
Carbon Bond ◽  
Carbonyl Derivatives ◽  
Carbon Carbon Bond ◽  
Transition Metal Catalyzed ◽  
Metal Catalyzed

α-Functionalization of carbonyl compounds in organic synthesis has traditionally been accomplished via classical enolate chemistry. As α-functionalized carbonyl moieties are ubiquitous in biologically and pharmaceutically valuable molecules, catalytic α-alkylations have been extensively studied, yielding a plethora of practical and efficient methodologies. Moreover, stereoselective carbon–carbon bond formation at the α-position of achiral carbonyl compounds has been achieved by using various transition metal–chiral ligand complexes. This review describes recent advances—in the last 20 years and especially focusing on the last 10 years—in transition metal-catalyzed α-alkylations of carbonyl compounds, such as aldehydes, ketones, imines, esters, and amides and in efficient carbon–carbon bond formations. Active catalytic species and ligand design are discussed, and mechanistic insights are presented. In addition, recently developed photo-redox catalytic systems for α-alkylations are described as a versatile synthetic tool for the synthesis of chiral carbonyl-bearing molecules.

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

Titanacyclopropanes as versatile intermediates for carbon-carbon bond formation in reactions with unsaturated compounds

2000 ◽  
Vol 72 (9) ◽  
pp. 1715-1719 ◽  
Author(s):  
O. G. Kulinkovich
Keyword(s):  
Reaction Mechanism ◽  
Bond Formation ◽  
Grignard Reagents ◽  
Allylic Alcohols ◽  
Ethylmagnesium Bromide ◽  
Carbon Bond ◽  
Unsaturated Compounds ◽  
Carbon Carbon Bond ◽  
Reaction Proceeds

Dialkoxytitanacyclopropane intermediates [or titanium (II)-olefin complexes] generated in situ from ethylmagnesium bromide and titanium (IV) isopropoxide react with allylic alcohols and allylic ethers to afford SN2' allylic ethylation products. The reaction proceeds with high regioselectivity and with low to high trans-/cis-stereoselectivity. This observation and others suggest a reaction mechanism involving an EtMgBr-initiated formation of titanacyclopentane ate complex 10 from titanacyclopropane-olefin complex 7 as a key step. Based on this assumption, a modified mechanism of titanium-mediated cyclopropanation of esters with Grignard reagents is proposed.

Carbon-Carbon Bond Formation: Palladium-Catalyzed Oxidative Cross-Coupling of N-Tosylhydrazones with Allylic Alcohols

2012 ◽  
Vol 18 (34) ◽  
pp. 10497-10500 ◽  
Author(s):  
Huoji Chen ◽  
Li Huang ◽  
Wei Fu ◽  
Xiaohang Liu ◽  
Huanfeng Jiang
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Allylic Alcohols ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed
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