Imino-ene reaction of N-tosyl arylaldimines with α-methylstyrene:: application in the synthesis of important amines

被引：31

作者：

Pandey, MK ^{[1
]}

Bisai, A ^{[1
]}

Pandey, A ^{[1
]}

Singh, VK ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 30期

关键词：

imino-ene reaction; Lewis acids; homoallylic amines;

D O I：

10.1016/j.tetlet.2005.05.073

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Copper(II) or tin(II) trifluoromethanesulfonate in combination with TMSCl effectively activates a C-H bond for the imino-ene reaction of N-tosylarylaldimines with alpha-methylstyrene. A wide variety of N-tosylarylaldimines were used to give homoallylamines in good to excellent yields under mild conditions. The imino-ene adduct was converted into a beta-amino ketone. The synthesis of a 2,4-substituted pyrrolidine and a piperidine was also achieved from the imino-ene product via a Mitsunobu reaction and a Grubbs cyclization, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：5039 / 5041

页数：3

共 31 条

[1] APPLICATION OF A NOVEL IMINO-ENE REACTION TO THE SYNTHESIS OF THE UNUSUAL MARINE ALKALOID PAPUAMINE
BORZILLERI, RM
WEINREB, SM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 211 - ORGN
[2] Stereoselective Synthesis of Tetrahydroquinolines Through an Imino-Ene Cyclization Reaction
Bondalapati, Somasekhar
Indukuri, Kiran
Ghosh, Priya
Saikia, Anil K.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (05) : 952 - 956
[3] Synthesis and Application of N-Tosyl Piperidinyl-Containing α-Aminophosphonates
Jiang, Zhifu
Zhao, Jian
Gao, Beibei
Chen, Shuo
Qu, Wenyan
Mei, Xiangdong
Rui, Changhui
Ning, Jun
She, Dongmei
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2013, 188 (08) : 1026 - 1037
[4] A 2-STEP PROCEDURE FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE N-TOSYL HOMOALLYLIC AMINES
BERRY, MB
CRAIG, D
JONES, PS
SYNLETT, 1993, (07) : 513 - 514
[5] Synthesis of N-Tosyl Allylic Amines from Substituted Alkenes via Vanadoxaziridine Catalysis
Madiu, Rufai
Doran, Erin L.
Doran, Jenna M.
Pinarci, Ali A.
Dhillon, Kiran
Rivera, Dominic A.
Howard, Amari M.
Stroud, James L.
Moskovitz, Dylan A.
Finneran, Steven J.
Singer, Alyssa N.
Rossi, Morgan E.
Moura-Letts, Gustavo
JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (06): : 4001 - 4008
[6] Synthesis of β-aryl substituted N-tosyl Aza-Baylis-Hillman adducts: Heck reaction of N-tosyl Aza-Baylis-Hillman adducts
Department of Chemistry, Institute of Basic Science, Chonnam National University, Gwangju 500-757, Korea, Republic of
Bull. Korean Chem. Soc., 2008, 8 (1583-1586):
[7] Synthesis of β-aryl substituted N-tosyl aza-Baylis-Hillman adducts:: Heck reaction of N-tosyl aza-Baylis-Hillman adducts
Kim, Jeong Mi
Kim, Sung Hwan
Kim, Se Hee
Kim, Jae Nyoung
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (08): : 1583 - 1586
[8] Enantioselective Imino-Ene Reaction of N-Sulfonyl Ketimines with Silyl Enol Ethers: Access to Chiral Benzosultams
Hou, Liuzhen
Kang, Tengfei
Yang, Liangkun
Cao, Weidi
Feng, Xiaoming
ORGANIC LETTERS, 2020, 22 (04) : 1390 - 1395
[9] RECOVERABLE AND REUSABLE CATALYST FOR THE REACTION OF N-TOSYL IMINES WITH PYRROLE: SYNTHESIS OF MESO-TETRAARYLPORPHYRINS
Temelli, Baris
Ozdemir, Saadet Seyma
HETEROCYCLES, 2012, 85 (04) : 851 - 860
[10] Palladium-catalyzed three-component reaction of N-tosyl hydrazones, isonitriles and amines leading to amidines
Dai, Qiang
Jiang, Yan
Yu, Jin-Tao
Cheng, Jiang
CHEMICAL COMMUNICATIONS, 2015, 51 (93) : 16645 - 16647

← 1 2 3 4 →