Direct Asymmetric Mannich-Type Reaction of α-Isocyanoacetates with Ketimines using Cinchona Alkaloid/Copper(II) Catalysts

2014 ◽  
Vol 126 (32) ◽  
pp. 8551-8555 ◽  
Author(s):  
Masashi Hayashi ◽  
Masaru Iwanaga ◽  
Noriyuki Shiomi ◽  
Daisuke Nakane ◽  
Hideki Masuda ◽  
...  
Keyword(s):  
Cinchona Alkaloid ◽  
Type Reaction

Construction of Multiple Stereocenters

2017 ◽  
Author(s):  
Léa Benkoski ◽  
Tristan H. Lambert
Keyword(s):  
Acid Derivative ◽  
Cinchona Alkaloid ◽  
Amino Acid Derivative ◽  
Iridium Complex ◽  
Max Planck ◽  
One Pot ◽  
Engineering Research ◽  
Type Reaction ◽  
Enantioselective Epoxidation ◽  
The University

Erick M. Carreira at ETH Zürich reported (Science 2013, 340, 1065) the enantiose­lective α-allylation of aldehyde 1 with alcohol 2 to produce 3 using a dual catalytic system involving a chiral iridium complex and amine 5. This stereodivergent method allows access to all of the possible stereoisomers of 3. In a conceptually related proc­ess, John F. Hartwig at the University of California, Berkeley reported (J. Am. Chem. Soc. 2013, 135, 2068) the highly stereoselective allylic alkylation of azlactone 6 with allylic carbonate 7 catalyzed by a combination of Ir(cod)Cl₂, ligand 9, and racemic silver phosphate 10. An enantioselective three-component Mannich-type reaction of tert-butyl diazo­acetate, aniline, and imine 11 to produce α,β-bis(arylamino) acid derivative 13 under dual catalysis with Rh₂(OAc)₄ and acid 12 was developed (Synthesis 2013, 45, 452) by Wenhao Hu at the Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development. Keiji Maruoka at Kyoto University reported (Chem. Commun. 2013, 49, 1118) a one-pot cross double-Mannich reaction of acetylalde­hyde 14, and imines 16 and 17 using axially chiral amino sulfonamide 15 to obtain densely functionalized 1,3-diamine 18 as a single stereoisomer. Jeffrey S. Johnson at the University of North Carolina at Chapel Hill reported (Org. Lett. 2013, 15, 2446) the asymmetric synthesis of enantioenriched anti-α-hydroxy-β-amino acid derivative 21 from 19 by treatment with oxone followed by catalytic hydrogenation using Ru(II) complex 20. Naoya Kumagai and Masakatsu Shibasaki at the Institute of Microbial Chemistry found (Org. Lett. 2013, 15, 2632) that a sil­ver complex of bisphosphine 24 effected a syn-selective and highly enantioselective Mannich-type reaction of aldimine 22 and α-sulfanyl lactone 23 to furnish the stereo­diad 25 with very high ee. The enantioselective homocrotylation of octanal 26 with cyclopropylcarbinylbo­ronate 27 to produce alcohol 28 with high ee was disclosed (J. Am. Chem. Soc. 2013, 135, 82) by Isaac J. Krauss at Brandeis University with computational studies pro­vided by Kendall N. Houk at UCLA. Benjamin List at the Max-Planck-Institut für Kohlenforschung reported (J. Am. Chem. Soc. 2013, 135, 6677) the enantioselective epoxidation of cyclohexenone 29 utilizing cinchona alkaloid- derived catalyst 30.

ChemInform Abstract: Cinchona Alkaloid Catalyzed Enantioselective Direct Aldol-Type Reaction of Oxinoles with Ethyl Trifluoropyruvate.

ChemInform ◽  
2008 ◽  
Vol 39 (13) ◽  
Author(s):  
Shinichi Ogawa ◽  
Norio Shibata ◽  
Junji Inagaki ◽  
Shuichi Nakamura ◽  
Takeshi Toru ◽  
...  
Keyword(s):  
Cinchona Alkaloid ◽  
Type Reaction

Cinchona Alkaloid-Catalyzed Enantioselective Monofluoromethylation Reaction Based on Fluorobis(phenylsulfonyl)methane Chemistry Combined with a Mannich-type Reaction

2007 ◽  
Vol 129 (20) ◽  
pp. 6394-6395 ◽  
Author(s):  
Satoshi Mizuta ◽  
Norio Shibata ◽  
Yosuke Goto ◽  
Tatsuya Furukawa ◽  
Shuichi Nakamura ◽  
...  
Keyword(s):  
Cinchona Alkaloid ◽  
Type Reaction

ChemInform Abstract: Direct Asymmetric Mannich-Type Reaction of α-Isocyanoacetates with Ketimines Using Cinchona Alkaloid/Copper(II) Catalysts.

ChemInform ◽  
2015 ◽  
Vol 46 (7) ◽  
pp. no-no
Author(s):  
Masashi Hayashi ◽  
Masaru Iwanaga ◽  
Noriyuki Shiomi ◽  
Daisuke Nakane ◽  
Hideki Masuda ◽  
...  
Keyword(s):  
Cinchona Alkaloid ◽  
Type Reaction

Direct Asymmetric Mannich-Type Reaction of α-Isocyanoacetates with Ketimines using Cinchona Alkaloid/Copper(II) Catalysts

2014 ◽  
Vol 53 (32) ◽  
pp. 8411-8415 ◽  
Author(s):  
Masashi Hayashi ◽  
Masaru Iwanaga ◽  
Noriyuki Shiomi ◽  
Daisuke Nakane ◽  
Hideki Masuda ◽  
...  
Keyword(s):  
Cinchona Alkaloid ◽  
Type Reaction

scholarly journals Cinchona Alkaloid-Catalyzed Enantioselective Monofluoromethylation Reaction Based on Fluorobis(phenylsulfonyl)methane Chemistry Combined with a Mannich-Type Reaction.

ChemInform ◽  
2007 ◽  
Vol 38 (39) ◽  
Author(s):  
Satoshi Mizuta ◽  
Norio Shibata ◽  
Yosuke Goto ◽  
Tatsuya Furukawa ◽  
Shuichi Nakamura ◽  
...  
Keyword(s):  
Cinchona Alkaloid ◽  
Type Reaction

Cinchona-Alkaloid-Catalyzed Enantioselective Direct Aldol-Type Reaction of Oxindoles with Ethyl Trifluoropyruvate

2007 ◽  
Vol 46 (45) ◽  
pp. 8666-8669 ◽  
Author(s):  
Shinichi Ogawa ◽  
Norio Shibata ◽  
Junji Inagaki ◽  
Shuichi Nakamura ◽  
Takeshi Toru ◽  
...  
Keyword(s):  
Cinchona Alkaloid ◽  
Type Reaction
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