Stereodefined N,O-Acetals: Pd-Catalyzed Synthesis from Homopropargylic Amines and Utility in the Flexible Synthesis of 2,6-Substituted Piperidines

被引：104

作者：

Kim, Haejin ^{[1
]}

Rhee, Young Ho ^{[1
]}

机构：

[1] Pohang Univ Sci & Technol, Dept Chem, Pohang 790784, Kyungbuk, South Korea

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 09期

基金：

新加坡国家研究基金会;

关键词：

ASYMMETRIC ALLYLIC ALKYLATION; GOLD(I)-CATALYZED INTRAMOLECULAR CARBOALKOXYLATION; RING-CLOSING METATHESIS; N-ACYLIMINIUM ION; INTERMOLECULAR HYDROAMINATION; PALLADIUM; GOLD; ALLENES; COMPLEXES; CHIRALITY;

D O I：

10.1021/ja2116298

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We developed a conceptually new synthetic strategy which exploits the stereochemical information of labile acyclic N,O-acetals. The key to this strategy, chemo- and stereoselective synthesis of N,O-acetals, was achieved by the Pd-catalyzed addition of sulfonyl-protected homopropargylic amines to alkoxyallene. The N,O-acetals generated in this way were combined with Au-catalyzed cycloisomerization to give an access to 2,6-disubstituted piperidines with stereochemical flexibility.

引用

页码：4011 / 4014

页数：4

共 46 条

[1] Use of group 4 bis(sulfonamido) complexes in the intramolecular hydroamination of alkynes and allenes [J].

Ackermann, L ;

Bergman, RG ;

Loy, RN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (39) :11956-11963

[2] Chirality Transfer in Au-Catalyzed Cyclization Reactions of Monoallylic Diols: Selective Access to Specific Enantiomers Based on Olefin Geometry [J].

Aponick, Aaron ;

Biannic, Berenger .

ORGANIC LETTERS, 2011, 13 (06) :1330-1333

[3] Enantioselective Decarboxylative Alkylation Reactions: Catalyst Development, Substrate Scope, and Mechanistic Studies [J].

Behenna, Douglas C. ;

Mohr, Justin T. ;

Sherden, Nathaniel H. ;

Marinescu, Smaranda C. ;

Harned, Andrew M. ;

Tani, Kousuke ;

Seto, Masaki ;

Ma, Sandy ;

Novak, Zoltan ;

Krout, Michael R. ;

McFadden, Ryan M. ;

Roizen, Jennifer L. ;

Enquist, John A., Jr. ;

White, David E. ;

Levine, Samantha R. ;

Petrova, Krastina V. ;

Iwashita, Akihiko ;

Virgil, Scott C. ;

Stoltz, Brian M. .

CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (50) :14199-14223

[4] Palladium-Catalyzed Regio-, Diastereo-, and Enantioselective Allylic Alkylation of Acylsilanes with Monosubstituted Allyl Substrates [J].

Chen, Jian-Ping ;

Ding, Chang-Hua ;

Liu, Wei ;

Hou, Xue-Long ;

Dai, Li-Xin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (44) :15493-15495

[5] Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].

Corma, A. ;

Leyva-Perez, A. ;

Sabater, Maria J. .

CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712

[6] Palladium heteroannulation process for synthesis of substituted pyrrolo [2,3-b]pyridin-3-ones [J].

Desarbre, E ;

Merour, JY .

TETRAHEDRON LETTERS, 1996, 37 (01) :43-46

[7] Flexible metathesis-based approaches to highly functionalised furans and pyrroles [J].

Donohoe, Timothy J. ;

Kershaw, Neil M. ;

Orr, Allan J. ;

Wheelhouse , Katherine M. P. ;

Fishlock, Lisa P. ;

Lacy, Adam R. ;

Bingham, Matilda ;

Procopiou, Panayiotis A. .

TETRAHEDRON, 2008, 64 (05) :809-820

[8] A metathesis approach to aromatic heterocycles [J].

Donohoe, TJ ;

Orr, AJ ;

Gosby, K ;

Bingham, M .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (10) :1969-1971

[9] Synthesis of indenyl ethers by gold(I)-catalyzed intramolecular carboalkoxylation of alkynes [J].

Dube, Pascal ;

Toste, F. Dean .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (37) :12062-12063

[10] Gold and platinum catalysis-a convenient tool for generating molecular complexity [J].

Fuerstner, Alois .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :3208-3221

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