Efficient 1,8- to 1,12-asymmetric induction in Grignard reactions of ω-keto esters by using BINOL or its 2′-oligoether derivatives as the chiral auxiliary

1999 ◽  
pp. 1141-1142 ◽  
Author(s):  
Yasufumi Tamai ◽  
Tetsutaro Hattori ◽  
Masamitsu Date ◽  
Hideki Takayama ◽  
Yoshinori Kamikubo ◽  
...  
Keyword(s):  
Chiral Auxiliary ◽  
Asymmetric Induction ◽  
Keto Esters ◽  
Grignard Reactions

ChemInform Abstract: Efficient 1,8- to 1,12-Asymmetric Induction in Grignard Reactions of ω-Keto Esters by Using BINOL or Its 2′-Oligoether Derivatives as the Chiral Auxiliary.

ChemInform ◽  
2010 ◽  
Vol 30 (39) ◽  
pp. no-no
Author(s):  
Yasufumi Tamai ◽  
Tetsutaro Hattori ◽  
Masamitsu Date ◽  
Hideki Takayama ◽  
Yoshinori Kamikubo ◽  
...  
Keyword(s):  
Chiral Auxiliary ◽  
Asymmetric Induction ◽  
Keto Esters ◽  
Grignard Reactions

Photochemistry of 9-methylbicyclo[3.3.1]nonyl aryl ketones — A novel 1,5-disproportionation of 1,4-hydroxy biradicals and asymmetric induction using the solid-state ionic chiral auxiliary method

2005 ◽  
Vol 83 (9) ◽  
pp. 1460-1472 ◽  
Author(s):  
Shuang Chen ◽  
Brian O Patrick ◽  
John R Scheffer
Keyword(s):  
Solid State ◽  
Single Crystal ◽  
Solid State Ionic ◽  
Chiral Auxiliary ◽  
Asymmetric Induction ◽  
X Ray Crystallography ◽  
Aryl Ketones ◽  
Hydroxy Biradicals ◽  
Phenyl Ketones ◽  
State Ionic

A novel 1,5-disproportionation reaction has been discovered for 1,4-hydroxy biradicals derived from the photolysis of 9-methylbicyclo[3.3.1]nonyl phenyl ketones (1), which undergo mainly Yang cyclization both in solution and the solid state. By applying the solid-state ionic chiral auxiliary method of asymmetric synthesis to the Yang cyclization, enantiomeric excesses as high as 95% were achieved at high reaction conversions. The origin of the reaction selectivity is discussed with the help of X-ray crystallography. In addition, the solid-state photoreaction of ketone 1b was found to occur in a single crystal-to-single crystal fashion.Key words: photochemistry, 1,4-hydroxy biradical, disproportionation, asymmetric induction, ionic chiral auxiliary, single crystal-to-single crystal reaction.

scholarly journals Asymmetric Electrophilic Difluoromethylthiolation of Indanone-Based β-Keto Esters Using Difluoromethanesulfonyl Hypervalent Iodonium Ylides

Molecules ◽  
2019 ◽  
Vol 24 (2) ◽  
pp. 221 ◽  
Author(s):  
Satoshi Gondo ◽  
Okiya Matsubara ◽  
Hélène Chachignon ◽  
Yuji Sumii ◽  
Dominique Cahard ◽  
...  
Keyword(s):  
Chiral Auxiliary ◽  
Direct Introduction ◽  
Keto Esters ◽  
Iodonium Ylides

The first electrophilic diastereoselective direct introduction of the difluoromethylthio group is described. We used a chiral auxiliary-based approach to illustrate the versatility of our recently developed difluoromethanesulfonyl hypervalent iodonium ylide reagents for the difluoromethylthiolation of indanone-based β-keto esters. Chiral SCF2H-featuring compounds were obtained in up to 93% ee value.

Asymmetric Induction in Darzens Condensation by Means of (R)-5,5- Dimethyl-4-Phenyloxazolidin-2-One as an Effective Chiral Auxiliary

2007 ◽  
Vol 4 (4) ◽  
pp. 228-231 ◽  
Author(s):  
Abed Badrian ◽  
Manouchehr Mamaghani ◽  
Khalil Tabatabaeian ◽  
Hassan Valizadeh
Keyword(s):  
Chiral Auxiliary ◽  
Asymmetric Induction ◽  
Darzens Condensation

ChemInform Abstract: Asymmetric Induction in the Darzens Reaction by Using an η6-Cr(CO)3 Complexed Arene as Chiral Auxiliary.

ChemInform ◽  
1987 ◽  
Vol 18 (47) ◽  
Author(s):  
C. BALDOLI ◽  
P. DEL BUTTERO ◽  
E. LICANDRO ◽  
S. MAIORANA ◽  
A. PAPAGNI
Keyword(s):  
Chiral Auxiliary ◽  
Asymmetric Induction ◽  
Darzens Reaction

Stereochemistry of grignard reactions on some conformationally mobile δ-keto esters

Tetrahedron ◽  
1978 ◽  
Vol 34 (3) ◽  
pp. 357-362 ◽  
Author(s):  
A Colantoni ◽  
G Di Maio ◽  
E Vecchi ◽  
E Zeuli ◽  
C Quagliata
Keyword(s):  
Keto Esters ◽  
Grignard Reactions
Sign in / Sign up

Export Citation Format

Share Document