Copper-Catalyzed Asymmetric Propargylation of Cyclic Aldimines

被引：50

作者：

Fandrick, Daniel R. ^{[1
]}

Hart, Christine A. ^{[2
]}

Okafor, Ifeanyi S. ^{[1
]}

Mercadante, Michael A. ^{[1
]}

Sanyal, Sanjit ^{[1
]}

Masters, James T. ^{[1
]}

Sarvestani, Max ^{[1
]}

Fandrick, Keith R. ^{[1
]}

Stockdill, Jennifer L. ^{[2
]}

Grinberg, Nelu ^{[1
]}

Gonnella, Nina ^{[1
]}

Lee, Heewon ^{[1
]}

Senanayake, Chris H. ^{[1
]}

机构：

[1] Boehringer Ingelheim Pharmaceut Inc, Chem Dev & Mat & Analyt Sci, 900 Old Ridgebury Rd,POB 368, Ridgefield, CT 06877 USA

[2] Wayne State Univ, Dept Chem, 5101 Cass Ave, Detroit, MI 48202 USA

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 23期

关键词：

ENANTIOSELECTIVE CARBONYL PROPARGYLATION; TETRAHYDRO-BETA-CARBOLINE; ISOQUINOLINE ALKALOIDS; TRANSFER HYDROGENATION; IMINES; AMINES; KETONES; EFFICIENT; ALDEHYDES; HYDROAMINATION;

D O I：

10.1021/acs.orglett.6b03253

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The copper-catalyzed asymmetric propargylation of cyclic aldimines is reported. The influence of the imine trimer to inhibit the reaction was identified, and equilibrium constants between the monomer and trimer were determined for general classes of imines. Asymmetric propargylation of a diverse series of N-alkyl and N-aryl aldimines was achieved with good to high asymmetric induction. The utility was demonstrated by a titanium catalyzed hydroamination and reduction to generate the chiral indolizidines (-)-crispine A and (-)-harmicine.

引用

页码：6192 / 6195

页数：4

共 73 条

[51] Silver-Catalyzed Enantioselective Propargylation Reactions of N-Sulfonylketimines [J].

Osborne, Charlotte A. ;

Endean, Thomas B. D. ;

Jarvo, Elizabeth R. .

ORGANIC LETTERS, 2015, 17 (21) :5340-5343

[52] Allylation of Imines and Their Derivatives with Organoboron Reagents: Stereocontrolled Synthesis of Homoallylic Amines [J].

Ramadhar, Timothy R. ;

Batey, Robert A. .

SYNTHESIS-STUTTGART, 2011, (09) :1321-1346

[53] Chiral Bronsted Acid Catalyzed Enantioselective Propargylation of Aldehydes with Allenylboronate [J].

Reddy, Leleti Rajender .

ORGANIC LETTERS, 2012, 14 (04) :1142-1145

[54] Asymmetric Synthesis of Tetrahydro-β-carboline Alkaloids Employing Ellman's Chiral Auxiliary [J].

Reddy, N. Siva Senkar ;

Babu, R. Anji ;

Reddy, B. V. Subba .

SYNTHESIS-STUTTGART, 2016, 48 (07) :1079-1086

[55] DAS VERHALTEN DER TRIMEREN DES DELTA-1-PIPERIDEINS BEI DER DESTILLATION [J].

SCHOPF, C ;

ARM, H ;

KRIMM, H .

CHEMISCHE BERICHTE-RECUEIL, 1951, 84 (08) :690-699

[56] Identification of Modular Chiral Bisphosphines Effective for Cu(I)-Catalyzed Asymmetric Allylation and Propargylation of Ketones [J].

Shi, Shi-Liang ;

Xu, Li-Wen ;

Oisaki, Kounosuke ;

Kanai, Motomu ;

Shibasaki, Masakatsu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (19) :6638-+

[57] A concise asymmetric synthesis of 5,8-disubstituted indolizidine alkaloids. Total synthesis of (-)-indolizidine 209B [J].

Song, YC ;

Okamoto, S ;

Sato, F .

TETRAHEDRON LETTERS, 2002, 43 (48) :8635-8637

[58] Ligand-accelerated Enantioselective Propargylation of Aldehydes via Allenylzinc Reagents [J].

Trost, Barry M. ;

Ngai, Ming-Yu ;

Dong, Guangbin .

ORGANIC LETTERS, 2011, 13 (08) :1900-1903

[59] Asymmetric Nozaki-Hiyama Propargylation of Aldehydes: Enhancement of Enantioselectivity by Cobalt Co-Catalysis [J].

Usanov, Dmitry L. ;

Yamamoto, Hisashi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (44) :8169-8172

[60] A Robust, Efficient, and Highly Enantioselective Method for Synthesis of Homopropargyl Amines [J].

Vieira, Erika M. ;

Haeffner, Fredrik ;

Snapper, Marc L. ;

Hoveyda, Amir H. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (27) :6618-6621

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