The endo-aza-Michael addition in the synthesis of piperidines and pyrrolidines

被引：27

作者：

Bates, Roderick W. ^{[1
]}

Ko, Weiting ^{[1
]}

Barat, Viktor ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 05期

关键词：

DIELS-ALDER REACTIONS; CENTERED RADICAL CATIONS; FORMAL TOTAL-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; 2,6-DISUBSTITUTED PIPERIDINES; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; 1,5-HYDROGEN MIGRATION; AMINO-ACIDS;

D O I：

10.1039/c9ob02388g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular endo-aza-Michael additions are categorised in various ways. Firstly whether they are single or double reactions, secondly whether they are endo- or exo-activated (or both), thirdly whether the Michael acceptor is an alkene or an alkyne, and finally whether the product is a six or a five membered ring. Reactions in the various categories are illustrated by syntheses of piperidines and pyrrolidines, including a range of natural products. The question of the stereochemical outcome and whether it is understood is discussed.

引用

页码：810 / 829

页数：20

共 50 条

[21] (-)-sparteine mediated enantioselective synthesis of substituted piperidines and pyrrolidines.
Johnson, TA
Curtis, MD
Beak, P
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U73 - U73
[22] Nucleophilic synthesis of enantiopure 2-(tributylstannyl)pyrrolidines and piperidines
Gawley, RE
Barolli, G
Madan, S
Saverin, M
O'Connor, S
TETRAHEDRON LETTERS, 2004, 45 (08) : 1759 - 1761
[23] A new, simple synthesis of N-tosyl pyrrolidines and piperidines
Marcotullio, Maria Carla
Campagna, Valerio
Sternativo, Silvia
Costantino, Ferdinando
Curini, Massimo
SYNTHESIS-STUTTGART, 2006, (16): : 2760 - 2766
[24] Highly enantio- and diastereoselective organocatalytic cascade aza-Michael-Michael reactions: a direct method for the synthesis of trisubstituted chiral pyrrolidines
Li, Hao
Zu, Liansuo
Xie, Hexin
Wang, Jian
Wang, Wei
CHEMICAL COMMUNICATIONS, 2008, (43) : 5636 - 5638
[25] Asymmetric synthesis of α-substituted β-amino sulfones by aza-Michael addition α-alkylation
Enders, D
Müller, SF
Raabe, G
SYNLETT, 1999, (06) : 741 - 743
[26] Synthesis of highly substituted tetrahydroquinolines using ethyl cyanoacetate via aza-Michael-Michael addition
Palanimuthu, Arunan
Chen, Chinpiao
Lee, Gene-Hsian
RSC ADVANCES, 2020, 10 (23) : 13591 - 13600
[27] Diastereoselective aza-Michael addition for synthesis of carbohydrate-derived spiropiperazinones
Jevgeņija Lugiņina
Deniss Vasiļjevs
Ilgvalds Ivanovs
Anatoly Mishnev
Māris Turks
Monatshefte für Chemie - Chemical Monthly, 2019, 150 : 21 - 28
[28] Synthesis of Multisubstituted Tetrahydroquinolines through Aza-Michael/Michael Addition Catalyzed by Quaternary Ammonium Salt
Zhang, Li
Li, Yajun
Yuan, Yafen
Zhang, Bin
Gao, Yuan
Wu, Yongming
Song, Liping
SYNLETT, 2014, 25 (12) : 1781 - 1785
[29] Organocatalytic Enantioselective Cascade Aza-Michael/Michael Addition for the Synthesis of Highly Functionalized Tetrahydroquinolines and Tetrahydrochromanoquinolines
Yang, Wen
He, Hai-Xiao
Gao, Yu
Du, Da-Ming
ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3670 - 3678
[30] Diastereoselective aza-Michael addition for synthesis of carbohydrate-derived spiropiperazinones
Luginina, Jevgenija
Vasiljevs, Deniss
Ivanovs, Ilgvalds
Mishnev, Anatoly
Turks, Maris
MONATSHEFTE FUR CHEMIE, 2019, 150 (01): : 21 - 28

← 1 2 3 4 5 →