A highly enantioselective Mannich reaction of aldehydes with cyclic N-acyliminium ions by synergistic catalysis

被引：39

作者：

Berti, Francesco ^{[1
]}

Malossi, Federico ^{[1
]}

Marchetti, Fabio ^{[2
]}

Pineschi, Mauro ^{[1
]}

机构：

[1] Univ Pisa, Dipartimento Farm, Sede Chim Bioorgan & Biofarm, I-56126 Pisa, Italy

[2] Univ Pisa, Dipartimento Chim & Chim Ind, I-56124 Pisa, Italy

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 71期

关键词：

ASYMMETRIC-SYNTHESIS; DERIVATIVES; PIPERIDINES; ALKALOIDS; SALTS; METHYLPHENIDATE; ISOQUINOLINES; QUINOLINES; ARYLATION; REAGENTS;

D O I：

10.1039/c5cc04416b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Matched combinations of Bronsted or Lewis acids with suitable pro-electrophiles and secondary amine organocatalysts enable the novel enantioselective syntheses of carbamoyl dihydroquinoline and tetrahydropyridine derivatives with concomitant formation of two stereocenters. A short formal asymmetric synthesis of (2R, 2'R)-threo-methylphenidate (Ritalin) is also described.

引用

页码：13694 / 13697

页数：4

共 26 条

[1] Synergistic catalysis: A powerful synthetic strategy for new reaction development [J].

Allen, Anna E. ;

MacMillan, David W. C. .

CHEMICAL SCIENCE, 2012, 3 (03) :633-658

[2] Copper-catalyzed coupling of pyridines and quinolines with alkynes: A one-step, asymmetric route to functionalized heterocycles [J].

Black, Daniel A. ;

Beveridge, Ramsay E. ;

Arndtsen, Bruce A. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1906-1910

[3] Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode [J].

Chau, Stephen T. ;

Lutz, J. Patrick ;

Wu, Kevin ;

Doyle, Abigail G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9153-9156

[4] Copper-Catalyzed Perkin-Acyl-Mannich Reaction of Acetic Anhydride with Pyridine: Expeditious Entry to Unconventional Piperidines [J].

Crotti, Stefano ;

Berti, Francesco ;

Pineschi, Mauro .

ORGANIC LETTERS, 2011, 13 (19) :5152-5155

[5] Highly regio-, diastereo-, and enantioselective C-H insertions of methyl aryldiazoacetates into cyclic N-BOC-protected amines.: Asymmetric synthesis of novel C2-symmetric amines and threo-methylphenidate [J].

Davies, HML ;

Hansen, T ;

Hopper, DW ;

Panaro, SA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (27) :6509-6510

[6] Combining transition metal catalysis and organocatalysis - an update [J].

Du, Zhenting ;

Shao, Zhihui .

CHEMICAL SOCIETY REVIEWS, 2013, 42 (03) :1337-1378

[7] Catalytic Enantioselective Addition of Dialkylzinc Reagents to N-Acylpyridinium Salts [J].

Fernandez-Ibanez, M. Angeles ;

Macia, Beatriz ;

Pizzuti, Maria Gabriella ;

Minnaard, Adriaan J. ;

Feringa, Ben L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9339-9341

[8] Stereoselective Organocatalytic Addition of Nucleophiles to Isoquinolinium and 3,4-dihydroisoquinolinium Ions: A Simple Approach for the Synthesis of Isoquinoline Alkaloids [J].

Gualandi, Andrea ;

Mengozzi, Luca ;

Manoni, Elisabetta ;

Cozzi, Pier Giorgio .

CATALYSIS LETTERS, 2015, 145 (01) :398-419

[9] Synergy, Compatibility, and Innovation: Merging Lewis Acids with Stereoselective Enamine Catalysis [J].

Gualandi, Andrea ;

Mengozzi, Luca ;

Wilson, Claire M. ;

Cozzi, Pier Giorgio .

CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (04) :984-995

[10] What is your actual catalyst? TMS cleavage rates of diarylprolinol silyl ethers studied by in situ NMR [J].

Haindl, Michael H. ;

Schmid, Markus B. ;

Zeitler, Kirsten ;

Gschwind, Ruth M. .

RSC ADVANCES, 2012, 2 (14) :5941-5943

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