Chiral amine-catalyzed asymmetric conjugate addition of aldehydes to α-phenylselenoenones as formal Z-allylating agents

2018 ◽  
Vol 54 (2) ◽  
pp. 176-179 ◽  
Author(s):  
Taichi Kano ◽  
Hiroki Maruyama ◽  
Chihiro Homma ◽  
Keiji Maruoka
Keyword(s):  
Conjugate Addition ◽  
Chiral Amine

α-Selenoenones could be employed as Z-allyl precursors in the chiral amine-catalyzed asymmetric conjugate addition of aldehydes.

Regio- and Stereoselective Conjugate Addition of Aldehydes to β-Tosyl Enones under the Catalysis of a Binaphthyl-Modified Chiral Amine

2015 ◽  
Vol 54 (29) ◽  
pp. 8462-8465 ◽  
Author(s):  
Taichi Kano ◽  
Hisashi Sugimoto ◽  
Hiroki Maruyama ◽  
Keiji Maruoka
Keyword(s):  
Conjugate Addition ◽  
Chiral Amine

scholarly journals Stereoselective synthesis of perillaldehyde-based chiral β-amino acid derivatives through conjugate addition of lithium amides

2014 ◽  
Vol 10 ◽  
pp. 2738-2742 ◽  
Author(s):  
Zsolt Szakonyi ◽  
Reijo Sillanpää ◽  
Ferenc Fülöp
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Minor Component ◽  
Conjugate Addition ◽  
Building Blocks ◽  
Major Product ◽  
Amino Ester ◽  
Chiral Amine ◽  
Amino Esters ◽  
Lithium Amides

The Michael addition of dibenzylamine to (+)-tert-butyl perillate (3) and to (+)-tert-butyl phellandrate (6), derived from (S)-(−)-perillaldehyde (1), resulted in diastereomeric β-amino esters 7A–D in a moderately stereospecific reaction in a ratio of 76:17:6:1. After separation of the diastereoisomers, the major product, cis isomer 7A, was quantitatively isomerized to the minor component, trans-amino ester 7D. All four isomers were transformed to the corresponding β-amino acids 10A–D, which are promising building blocks for the synthesis of β-peptides and 1,3-heterocycles in three steps. The steric effects of the isopropyl group at position 4 and of the α-methyl substituent of (R)-N-benzyl-N-α-methylbenzylamine on the reactivity were also studied and, upon application of a chiral amine, excellent stereoselectivity of the conjugate addition was observed. Amino ester 11 was obtained as a single product and transformed to the corresponding amino acids 10A and 10D in good yields on the gram scale.

Enantioselective Preparation of Alcohols and Amines: The Lam Synthesis of (+)-Tanikolide

2013 ◽  
Author(s):  
Douglass F. Taber
Keyword(s):  
Amino Acids ◽  
Conjugate Addition ◽  
Allylic Alcohol ◽  
University Of Virginia ◽  
Chiral Amine ◽  
Aliphatic Aldehydes ◽  
Nucleophilic Rearrangement ◽  
Silyl Acetals ◽  
Institute Of Technology ◽  
The University

Takashi Ooi of Nagoya University effected (J. Am. Chem. Soc. 2010, 132, 12240) the enantioselective protonation of ketene silyl acetals such as 1 to give 2 in high ee. Hyeon-Kyu Lee of the Korean Research Institute of Chemical Technology achieved (Org. Lett. 2010, 12, 4184) high ee in the hydrogenation of the cyclic sulfamidate 3 to 4. Doo Ok Jang of Yonsei University combined (J. Am. Chem. Soc. 2010, 132, 12168) the nucleophilic allyl indium with a protonated chiral amine to effect homologation of 5 to 6. Ryo Shintani and Tamio Hayashi of Kyoto University reported (Org. Lett. 2010, 12, 4106) a related advance with tetraarylborates. Kazuaki Ishihara, also of Nagoya University (Org. Lett. 2010, 12, 3502) and Yoshihiro Sohtome and Kazuo Nagasawa of the Tokyo University of Agriculture and Technology (Angew. Chem. Int. Ed. 2010, 49, 9254) devised conditions for adding malonate to imines such as 7. Professors Shintani and Hayashi also employed (J. Am. Chem. Soc. 2010, 132, 13168) tetraarylborates to convert 9 to the α-quaternary amine 10. Professor Ooi (Angew. Chem. Int. Ed. 2010, 49, 5567) and Wanbin Zhang of Shanghai Jiao Tong University (J. Am. Chem. Soc. 2010, 132, 15939) prepared α-quaternary amino acids such as 12 by nucleophilic rearrangement of 11. Keiji Maruoka, also of Kyoto University, reported (J. Am. Chem. Soc. 2010, 132, 17074; not illustrated) a catalytic enantioselective conjugate addition approach to α-quaternary amines. Shuji Akai of the University of Shizuoka converted (Org. Lett. 2010, 12, 4900) the racemic allylic alcohol 13 to the enantiomerically enriched acetate 14 by combining V-catalyzed equilibration with lipase-catalyzed acylation. Toshiro Harada of the Kyoto Institute of Technology added (Org. Lett. 2010, 12, 5270) the alkenylboron 16 to the aldehyde 15 with high ee. Xiang Zhou of Wuhan University and Lin Pu of the University of Virginia significantly improved (Tetrahedron Lett . 2010, 51, 5024) a protocol for the enantioselective addition of aliphatic alkynes to aliphatic aldehydes. For other enantioselective additions to aldehydes (not illustrated), see J. Org. Chem. 2010, 75 , 5326 and Org. Lett. 2010, 12, 5088.

ChemInform Abstract: Regio- and Stereoselective Conjugate Addition of Aldehydes to β-Tosyl Enones under the Catalysis of a Binaphthyl-Modified Chiral Amine.

ChemInform ◽  
2015 ◽  
Vol 46 (46) ◽  
pp. no-no
Author(s):  
Taichi Kano ◽  
Hisashi Sugimoto ◽  
Hiroki Maruyama ◽  
Keiji Maruoka
Keyword(s):  
Conjugate Addition ◽  
Chiral Amine

A Strategy Enabling Enantioselective Direct Conjugate Addition of Inert Aryl Methane Nucleophiles to Enals with a Chiral Amine Catalyst under Mild Conditions

2013 ◽  
Vol 19 (28) ◽  
pp. 9147-9150 ◽  
Author(s):  
Tengfei Li ◽  
Jin Zhu ◽  
Deyan Wu ◽  
Xiangmin Li ◽  
Sinan Wang ◽  
...  
Keyword(s):  
Conjugate Addition ◽  
Chiral Amine ◽  
Mild Conditions

Regio- and Stereoselective Conjugate Addition of Aldehydes to β-Tosyl Enones under the Catalysis of a Binaphthyl-Modified Chiral Amine

2015 ◽  
Vol 127 (29) ◽  
pp. 8582-8585 ◽  
Author(s):  
Taichi Kano ◽  
Hisashi Sugimoto ◽  
Hiroki Maruyama ◽  
Keiji Maruoka
Keyword(s):  
Conjugate Addition ◽  
Chiral Amine

Chiral Amine-Mediated Asymmetric Conjugate Additions to Vinyl Sulfones

2009 ◽  
Vol 62 (9) ◽  
pp. 951 ◽  
Author(s):  
Qiang Zhu ◽  
Yixin Lu
Keyword(s):  
Organic Synthesis ◽  
Recent Progress ◽  
Conjugate Addition ◽  
Chiral Molecules ◽  
Conjugate Additions ◽  
Chiral Amine ◽  
Michael Acceptors

Chiral molecules containing sulfone groups are useful intermediates and have found wide applications in organic synthesis. In this account, recent progress in the use of vinyl sulfones as Michael acceptors in the asymmetric organocatalytic conjugate addition is summarized.

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