Synthesis of Ar-BINMOL Ligands by [1,2]-Wittig Rearrangement to Probe Their Catalytic Activity in 1,2-Addition Reactions of Aldehydes with Grignard Reagents

2012 ◽  
Vol 2013 (4) ◽  
pp. 748-755 ◽  
Author(s):  
Long-Sheng Zheng ◽  
Ke-Zhi Jiang ◽  
Yuan Deng ◽  
Xing-Feng Bai ◽  
Guang Gao ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Grignard Reagents ◽  
Addition Reactions ◽  
Wittig Rearrangement

Asymmetric Addition Reactions of Grignard Reagents to Chiral 2-Trifluoromethyl tert-Butyl (Ellman) Sulfinimine—Ethanol Adducts.

ChemInform ◽  
2006 ◽  
Vol 37 (29) ◽  
Author(s):  
Scott D. Kuduk ◽  
Christina Ng Di Marco ◽  
Steven M. Pitzenberger ◽  
Nancy Tsou
Keyword(s):  
Grignard Reagents ◽  
Addition Reactions ◽  
Asymmetric Addition ◽  
Tert Butyl

Asymmetric Conjugate Addition of α-Cyanoketones to Benzoyl Acrylonitrile Derivatives Using a Diaminomethylenemalononitrile Organocatalyst

Synthesis ◽  
2020 ◽  
Vol 52 (24) ◽  
pp. 3874-3880 ◽  
Author(s):  
Tsuyoshi Miura ◽  
Hiroshi Akutsu ◽  
Kosuke Nakashima ◽  
Yuta Kanetsuna ◽  
Masahiro Kawada ◽  
...  
Keyword(s):  
Catalytic Activity ◽  
Conjugate Addition ◽  
Significant Loss ◽  
Addition Reactions ◽  
Dicarbonyl Compounds ◽  
Stereogenic Centers ◽  
Synthetic Intermediates ◽  
Quaternary Stereogenic Centers

AbstractA diaminomethylenemalononitrile (DMM) organocatalyst was used to efficiently promote asymmetric conjugate addition of various α-cyanoketones to benzoyl acrylonitrile derivatives. The corresponding 1,5-dicarbonyl compounds containing vicinal tertiary and quaternary stereogenic centers are versatile synthetic intermediates and were obtained in good yields and with excellent enantioselectivities (up to 96% ee). The present study describes the first successful examples of asymmetric conjugate addition reactions of α-cyanoketones with benzoyl acrylonitriles. In addition, the DMM organocatalyst can be recovered and reused up to five times without significant loss of either catalytic activity or enantioselectivity.

Asymmetric addition reactions of Grignard reagents to chiral 2-trifluoromethyl tert-butyl (Ellman) sulfinimine–ethanol adducts

2006 ◽  
Vol 47 (14) ◽  
pp. 2377-2381 ◽  
Author(s):  
Scott D. Kuduk ◽  
Christina Ng Di Marco ◽  
Steven M. Pitzenberger ◽  
Nancy Tsou
Keyword(s):  
Grignard Reagents ◽  
Addition Reactions ◽  
Asymmetric Addition ◽  
Tert Butyl

Stereochemistry of the Addition Reactions of Grignard Reagents to 20-Keto Steroids. Sythesis of 17.alpha.,20.alpha.--Dihydroxycholesterol

1969 ◽  
Vol 34 (12) ◽  
pp. 3759-3766 ◽  
Author(s):  
N. Chaudhuri ◽  
June Williams ◽  
Robert Nickolson ◽  
Marcel Gut
Keyword(s):  
Grignard Reagents ◽  
Addition Reactions
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