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.

ChemInform Abstract: NaBH4-MnCl2 for Improved Reduction of β-Keto Esters Attached to a Chiral Auxiliary. Comparison with Zn(BH4)2.

ChemInform ◽  
2010 ◽  
Vol 33 (52) ◽  
pp. no-no
Author(s):  
P. R. R. Costa ◽  
C. V. F. Lima ◽  
P. R. Paiva ◽  
S. Pinheiro
Keyword(s):  
Chiral Auxiliary ◽  
Keto Esters

NaBH4-MnCl2, FOR IMPROVED REDUCTION OF β-KETO ESTERS ATTACHED TO A CHIRAL AUXILIARY. COMPARISON WITH Zn(BH4)2

2002 ◽  
Vol 34 (5) ◽  
pp. 502-507 ◽  
Author(s):  
P. R. R. Costa ◽  
C. V. F. Lima ◽  
P. R. Paiva ◽  
S. Pinheiro
Keyword(s):  
Chiral Auxiliary ◽  
Keto Esters

scholarly journals Difluoromethanesulfonyl hypervalent iodonium ylides for electrophilic difluoromethylthiolation reactions under copper catalysis

2016 ◽  
Vol 3 (5) ◽  
pp. 160102 ◽  
Author(s):  
Sadayuki Arimori ◽  
Okiya Matsubara ◽  
Masahiro Takada ◽  
Motoo Shiro ◽  
Norio Shibata
Keyword(s):  
Copper Catalysis ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Enol Ethers ◽  
Silyl Enol Ethers ◽  
Keto Esters ◽  
Wide Range ◽  
Allyl Alcohols ◽  
High Yields ◽  
Iodonium Ylides

Difluoromethanesulfonyl hypervalent iodonium ylides 2 were developed as electrophilic difluoromethylthiolation reagents for a wide range of nucleophiles. Enamines, indoles, β-keto esters, silyl enol ethers and pyrroles were effectively reacted with 2 affording desired difluoromethylthio (SCF 2 H)-substituted compounds in good to high yields under copper catalysis. The reaction of allyl alcohols with 2 under the same conditions provided difluoromethylsulfinyl (S(O)CF 2 H) products in good yields. The difluoromethylthiolation of enamines is particularly effective with wide generality, thus the enamine method was nicely extended to the synthesis of a series of difluoromethythiolated cyclic and acyclic β-keto esters, 1,3-diketones, pyrazole and pyrimidine derivatives by a consecutive, two-step one-pot reaction using 2.

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