Organocatalytic asymmetric addition of alcohols to cyclic trifluoromethyl ketimines: highly enantioselective synthesis of chiral N,O-ketals

2016 ◽  
Vol 14 (26) ◽  
pp. 6193-6196 ◽  
Author(s):  
Ding Zhou ◽  
Xueting Yu ◽  
Jian Zhang ◽  
Wei Wang ◽  
Hexin Xie
Keyword(s):  
Enantioselective Synthesis ◽  
Asymmetric Addition ◽  
Enantioselective Addition

A highly enantioselective addition of alcohols to cyclic trifluoromethyl ketimines catalyzed by quinine-thiourea is developed.

Enantioselective Addition of Alkynyl Esters and Ethers to Aldehydes Catalyzed by a Cyclopropyl Amino Alcohol Based Zinc Catalyst

Synlett ◽  
2019 ◽  
Vol 31 (01) ◽  
pp. 60-64
Author(s):  
Yun Zhou ◽  
Lifeng Wang ◽  
Shuoning Li ◽  
Sijie Ma ◽  
Patrick J. Walsh ◽  
...  
Keyword(s):  
Functional Groups ◽  
Amino Alcohol ◽  
Carbon Chain ◽  
Enantioselective Synthesis ◽  
Asymmetric Addition ◽  
Enantioselective Addition

A novel and highly enantioselective synthesis of hydroxyalkynyl esters and ethers through the asymmetric addition of alkynyl esters or ethers to aldehydes promoted by a cyclopropyl amino alcohol based zinc catalyst has been developed. The method afforded a library of new enantioenriched hydroxyalkynol esters and ethers (up to 93% yield; 95% ee), and it was compatible with a broad range of functional groups. Moreover, it could be used in the synthesis of carbon-chain-elongated enantioenriched hydroxyalkynol esters and (2R,5R)-musclide-A1, a cardiotonic potentiating principle from musk.

Enantioselective synthesis of α,α-disubstituted α-amino acids via direct catalytic asymmetric addition of acetonitrile to α-iminoesters

2016 ◽  
Vol 14 (41) ◽  
pp. 9725-9730 ◽  
Author(s):  
Shaoquan Lin ◽  
Naoya Kumagai ◽  
Masakatsu Shibasaki
Keyword(s):  
Amino Acids ◽  
Enantioselective Synthesis ◽  
Asymmetric Addition ◽  
Carbene Complexes ◽  
Enantioselective Addition ◽  
Catalytic Asymmetric

Chiral N-heterocyclic carbene complexes of [Ir(cod)(OMe)]2 in combination with Barton's base enabled direct enantioselective addition of acetonitrile to α-iminoesters.

Enantioselective Synthesis of Alkylated Centers: The Fukuyama Synthesis of (–)-Histrionicotoxin

2015 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Indian Institute ◽  
Enantioselective Synthesis ◽  
Max Planck ◽  
Dimethyl Malonate ◽  
Co Catalyst ◽  
Cu Catalyst ◽  
Enantioselective Addition ◽  
Institute Of Technology ◽  
Enantioselective Alkylation ◽  
Technological University

Vinod K. Singh of the Indian Institute of Technology, Kanpur optimized (Org. Lett. 2011, 13, 6520) an organocatalyst for the enantioselective addition of thiophenol to an imide 1 to give 2 in high ee. Amir H. Hoveyda of Boston College developed (Angew. Chem. Int. Ed. 2011, 50, 7079) a Cu catalyst for the preparation of 4 by the enantioselective hydroboration of a 1,1-disubstituted alkene 3. Yong-Qiang Tu of Lanzhou University effected (Chem. Sci. 2011, 2, 1839) enantioselective bromination of the prochiral 5 to give the bromoketone 6. Song Ye of the Institute of Chemistry, Beijing established (Chem. Commun. 2011, 47, 8388) the alkylated quaternary center of the dimer 8, by condensing a ketene 7 with CS2. Li Deng of Brandeis University added (Angew. Chem. Int. Ed. 2011, 50, 10565) cyanide in a conjugate sense to an acyl imidazole 9 to give 11. Pier Giorgio Cozzi of the Università di Bologna prepared (Angew. Chem. Int. Ed. 2011, 50, 7842) the thioacetal 14 by condensing 13 with an aldehyde 12, followed by reduction. Takahiro Nishimura and Tamio Hayashi of Kyoto University devised (Chem. Commun. 2011, 47, 10142) a Co catalyst for the enantioselective addition of a silyl alkyne 16 to an enone 15 to give the alkynyl ketone 17. Ping Tian and Guo-Qiang Lin of the Shanghai Institute of Organic Chemistry described (Tetrahedron 2011, 67, 10186) improved catalysts for the enantioselective conjugate addition of dimethyl malonate 19 to the nitroalkene 18, to give 20. Keiji Maruoka, also of Kyoto University, established (Chem. Sci. 2011, 2, 2311) conditions for the enantioselective addition of an aldehyde 21 to the acceptor 22 to give, after reduction, an alcohol 23 that could readily be cyclized to the lactone. Jianrong (Steve) Zhou of Nanyang Technological University prepared (J. Am. Chem. Soc. 2011, 133, 15882) the ester 26 by arylation, under Pd catalysis, of a ketene silyl acetal 24 with the triflate 25. Benjamin List of the Max-Planck-Institut, Mülheim employed (Angew. Chem. Int. Ed. 2011, 50, 9471) a system of three catalysts to effect the enantioselective alkylation of an aldehyde 27 with the allyic alcohol 28 to give 29.

Core-structure-inspired asymmetric addition reactions: enantioselective synthesis of dihydrobenzoxazinone- and dihydroquinazolinone-based anti-HIV agents

2015 ◽  
Vol 44 (21) ◽  
pp. 7439-7448 ◽  
Author(s):  
Shen Li ◽  
Jun-An Ma
Keyword(s):  
Asymmetric Synthesis ◽  
Core Structure ◽  
Enantioselective Synthesis ◽  
Addition Reactions ◽  
Asymmetric Addition ◽  
Anti Hiv Agents ◽  
Anti Hiv

An overview of the asymmetric synthesis of dihydrobenzoxazinone- and dihydroquinazolinone-based anti-HIV agents (Efavirenz, DPC 961, DPC 963, DPC 083) and analogues was presented.

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