The aza-Wittig reaction: an efficient tool for the construction of carbon-nitrogen double bonds

被引：382

作者：

Palacios, Francisco ^{[1
]}

Alonso, Concepcion ^{[1
]}

Aparicio, Dornitila ^{[1
]}

Rubiales, Gloria ^{[1
]}

de los Santos, Jesus M. ^{[1
]}

机构：

[1] Univ Basque Country, Fac Farm, Dept Quim Organ 1, Vitoria 01080, Spain

来源：

TETRAHEDRON | 2007年 / 63卷 / 03期

关键词：

D O I：

10.1016/j.tet.2006.09.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Recent advances in the aza-Wittig reaction of phosphazene derivatives with several carbonyl compounds are reviewed. Phosphazenes afford inter- and intramolecular aza-Wittig reactions with different compounds such as aldehydes, ketones, esters, thioesters, amides, anhydrides and sultimides. One of the most important applications of this reaction is the synthesis of a wide range of acyclic and heterocyclic compounds, ranging from simple monocyclic compounds to complex polycyclic and macrocyclic systems. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：523 / 575

页数：53

共 243 条

[31] Novel N-(2-benzo[b]thienyl)iminophosphoranes and their use in the synthesis of benzo[b]thieno[2,3-b]pyridines [J].

Bonini, C ;

D'Auria, M ;

Funicello, M ;

Romaniello, G .

TETRAHEDRON, 2002, 58 (18) :3507-3512

[32] N-(3-benzo[b]thienyl)iminophosphoranes toward the synthesis of benzo[b]thieno[3,2-b]pyridines:: Reactivity and alternative regioselectivity with α,β-unsaturated ketones and aldehydes [J].

Bonini, C ;

Chiummiento, L ;

Funicello, M ;

Spagnolo, P .

TETRAHEDRON, 2000, 56 (11) :1517-1521

[33] ALTERNATIVE PROCEDURES FOR THE MACROLACTAMIZATION OF OMEGA-AZIDO ACIDS [J].

BOSCH, I ;

ROMEA, P ;

URPI, F ;

VILARRASA, J .

TETRAHEDRON LETTERS, 1993, 34 (29) :4671-4674

[34] The behavior of N-phenyliminophosphorane towards o- and p-quinones.: New synthesis of dioxazole and oxadiazole derivatives [J].

Boulos, LS ;

Arsanious, MHN .

SYNTHETIC COMMUNICATIONS, 2002, 32 (18) :2779-2790

[35]

Bravo P, 1996, SYNLETT, P887

[36] On the fate of the tryptophan stereocenter during the synthesis of hexacyclic analogues of N-acetylardeemin [J].

Caballero, E ;

Avendaño, C ;

Menéndez, JC .

TETRAHEDRON-ASYMMETRY, 1998, 9 (17) :3025-3038

[37] Conversion of alcohols into N-alkyl anilines via an indirect aza-Wittig reaction [J].

Cami-Kobeci, G ;

Williams, JMJ .

CHEMICAL COMMUNICATIONS, 2004, (09) :1072-1073

[38] An Aza-Wittig/π-Furan cyclization approach toward the homoerythrina alkaloid (±)-selaginoidine [J].

Cassidy, MP ;

Özdemir, AD ;

Padwa, A .

ORGANIC LETTERS, 2005, 7 (07) :1339-1342

[39] Synthesis of a triphenylphosphine reagent on non-cross-linked polystyrene support: Application to the Staudinger/Aza-Wittig reaction [J].

Charette, AB ;

Boezio, AA ;

Janes, MK .

ORGANIC LETTERS, 2000, 2 (24) :3777-3779

[40] REACTIONS OF (VINYLIMINO)PHOSPHORANES AND RELATED-COMPOUNDS - ACCESS TO THE AZACARBOLINES AND APLYSINOPSINES [J].

CHAVIGNON, O ;

TEULADE, JC ;

ROCHE, D ;

MADESCLAIRE, M ;

BLACHE, Y ;

GUEIFFIER, A ;

CHABARD, JL ;

DAUPHIN, G .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6413-6418

← 1 2 3 4 5 6 7 8 9 10 →