ChemInform Abstract: Pseudo-Macrocyclic Chelation Control in Remote Asymmetric Induction. Highly Efficient 1,7-Asymmetric Inductive Hydride Reduction and Grignard Reaction of γ-Keto Esters of 1,1′-Binaphthalen-2-ols Bearing an Appropriate Oligoether Group

ChemInform ◽  
2010 ◽  
Vol 30 (44) ◽  
pp. no-no
Author(s):  
Yasufumi Tamai ◽  
Tetsutaro Hattori ◽  
Masamitsu Date ◽  
Shinji Koike ◽  
Yoshinori Kamikubo ◽  
...  
Keyword(s):  
Asymmetric Induction ◽  
Grignard Reaction ◽  
Keto Esters ◽  
Highly Efficient ◽  
Hydride Reduction

Preparation of β-Substituted γ-Keto Esters by the Grignard Reaction on N-Acylpyrazoles

Heterocycles ◽  
2001 ◽  
Vol 54 (1) ◽  
pp. 309 ◽  
Author(s):  
Choji Kashima ◽  
Yoshie Shirahata ◽  
Yoshihiro Tsukamoto
Keyword(s):  
Grignard Reaction ◽  
Keto Esters

ChemInform Abstract: Preparation of β-Substituted γ-Keto Esters by the Grignard Reaction on N-Acylpyrazoles.

ChemInform ◽  
2010 ◽  
Vol 32 (23) ◽  
pp. no-no
Author(s):  
Choji Kashima ◽  
Yoshie Shirahata ◽  
Yoshihiro Tsukamoto
Keyword(s):  
Grignard Reaction ◽  
Keto Esters

Synthesis oftrans- and cis-α-damascone

1978 ◽  
Vol 56 (10) ◽  
pp. 1368-1371 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Hing-Kwok Hung ◽  
George L. Mhehe ◽  
M. L. Duarte Weinberg
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Complete Recovery ◽  
Lithium Aluminum ◽  
Magnesium Bromide ◽  
Keto Ester ◽  
Keto Esters ◽  
Hydride Reduction ◽  
Cis And Trans ◽  
Cis Isomer

Se lective thioketalization of a mixture of keto esters 5 and 6 resulted in the exclusive formation of thioketal 7 and complete recovery of keto ester 6. Lithium aluminum hydride reduction of thioketal 7 followed by Moffatt oxidation of the resulting alcohol 8 gave aldehyde 10 which on treatment with a mixture of cis- and trans-1-propenyl magnesium bromide afforded trans- alcohol 11 and its cis isomer 12. Manganese dioxide oxidation of alcohol 11 followed by desulfurization gave trans α-damascone (3). Similarly, alcohol 12 was converted to cis-α-damascone (4).

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