A lactam-derived vinyl boronate as a stable and crystalline reagent for the synthesis of 2--substituted piperidines by Pd-catalyzed coupling reactions

被引：9

作者：

Ferrali, A ^{[1
]}

Guarna, A ^{[1
]}

Lo Galbo, F ^{[1
]}

Occhiato, EG ^{[1
]}

机构：

[1] Univ Florence, Dipartimento Chim Organ U Schiff, I-50019 Sesto Fiorentino, Italy

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 27期

关键词：

D O I：

10.1016/j.tetlet.2004.05.015

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A delta-valerolactam-derived vinyl triflate has been converted into the corresponding vinyl boronate by Pd-catalyzed coupling with bis(pinacolato)diboron, which results in all umpolung. This boronate efficiently couples under Pd catalysis with aryl and heteroaryl bromides to give the corresponding 2-substituted piperidines ill excellent yields. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5271 / 5274

页数：4

共 45 条

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Occhiato, EG
Prandi, C
Ferrali, A
Guarna, A
Deagostino, A
Venturello, P
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20): : 7144 - 7146
[2] Synthesis of a biotin-derived alkyne for Pd-catalyzed coupling reactions
Corona, C
Bryant, BK
Arterburn, JB
ORGANIC LETTERS, 2006, 8 (09) : 1883 - 1886
[3] Pd(0)-catalyzed cross-coupling reactions of boron derivatives with a lactam-derived N-Boc enol triflate
Occhiato, EG
Trabocchi, A
Guama, A
ORGANIC LETTERS, 2000, 2 (09) : 1241 - 1242
[4] On the scope of Pd-catalyzed carboamination reactions-synthesis of 2,4-disubstituted pyrrolidines and 2-substituted piperidines and morpholines
Jepsen, Tue Heesgaard
Larsen, Mogens
Nielsen, Mogens Brondsted
TETRAHEDRON, 2010, 66 (32) : 6133 - 6137
[5] Synthesis of 2-substituted benzo[b]thiophene via a Pd-catalyzed coupling of 2-iodothiophenol with phenylacetylene
Chen, Jingwen
Xiang, Haifeng
Yang, Li
Zhou, Xiangge
RSC ADVANCES, 2017, 7 (13): : 7753 - 7757
[6] Stereodefined N,O-Acetals: Pd-Catalyzed Synthesis from Homopropargylic Amines and Utility in the Flexible Synthesis of 2,6-Substituted Piperidines
Kim, Haejin
Rhee, Young Ho
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (09) : 4011 - 4014
[7] STEREOSELECTIVE SYNTHESIS OF 1-INDANYLIDENE SUBSTITUTED HETEROAROMATIC DERIVATIVES VIA PD-CATALYZED TANDEM INSERTION AND CROSS COUPLING REACTIONS
LUO, FT
WANG, RT
HETEROCYCLES, 1990, 31 (08) : 1543 - 1548
[8] Stereodefined N,O-acetals: Pd-catalyzed synthesis from homopropargylic amines and utility in the flexible synthesis of 2,6-substituted piperidines
Kim, Haejin
Rhee, Young Ho
Journal of the American Chemical Society, 2012, 134 (09): : 4011 - 4014
[9] Configurationally stable, enantioenriched organometallic nucleophiles in stereospecific Pd-catalyzed cross-coupling reactions: an alternative approach to asymmetric synthesis
Wang, Chao-Yuan
Derosa, Joseph
Biscoe, Mark R.
CHEMICAL SCIENCE, 2015, 6 (09) : 5105 - 5113
[10] Stereoselective Synthesis of Substituted 1,3-Oxazolidines via Pd-Catalyzed Carboamination Reactions of O-Vinyl-1, 2-Amino Alcohols
Ward, Amanda F.
Wolfe, John P.
ORGANIC LETTERS, 2011, 13 (17) : 4728 - 4731

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