A sulfur-containing diselenide as an efficient chiral reagent in asymmetric selenocyclization reactions

被引：49

作者：

Tiecco, M ^{[1
]}

Testaferri, L ^{[1
]}

Marini, F ^{[1
]}

Sternativo, S ^{[1
]}

Bagnoli, L ^{[1
]}

Santi, C ^{[1
]}

Temperini, A ^{[1
]}

机构：

[1] Univ Perugia, Dipartimento Chim & Tecnol Faramaco, Sez Chim Organ, I-06123 Perugia, Italy

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(01)00248-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Treatment of the di-2-[(IS)-1-(methylthio)ethyl]phenyl diselenide with bromine and silver triflate afforded the corresponding selenyl triflate which was used in situ as a strongly electrophilic selenium reagent to effect the asymmetric synthesis of oxygen- or nitrogen-containing heterocycles. Cyclic ethers, lactones, lactams or N-protected pyrrolidines have been prepared in good yield with complete regioselectivity and high diastereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1493 / 1502

页数：10

共 50 条

[1] Efficient asymmetric selenomethoxylation and selenohydroxylation of alkenes with a new sulfur containing chiral diselenide
Tiecco, M
Testaferri, L
Bagnoli, L
Marini, F
Temperini, A
Tomassini, C
Santi, C
[J]. TETRAHEDRON LETTERS, 2000, 41 (17) : 3241 - 3245
[2] Preparation of a new chiral non-racemic sulfur-containing diselenide and applications in asymmetric synthesis
Tiecco, M
Testaferri, L
Santi, C
Tomassini, C
Marini, F
Bagnoli, L
Temperini, A
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2002, 8 (05) : 1118 - 1124
[3] Preparation of a new chiral non-racemic sulfur-containing diselenide and applications in asymmetric synthesis
Tiecco, Marcello
Testaferri, Lorenzo
Santi, Claudio
Tomassini, Cristina
Marini, Francesca
Bagnoli, Luana
Temperini, Andrea
[J]. 2002, Wiley-VCH Verlag (08)
[4] Chiral sulfur-containing ligands for asymmetric catalysis
Pellissier, Helene
[J]. TETRAHEDRON, 2007, 63 (06) : 1297 - 1330
[5] Progress of organozinc reagents in asymmetric addition reactions catalyzed by sulfur-containing chiral ligands
Yang, Wang-Gui
Wu, Shuai
Shi, Min
[J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2007, 27 (02) : 197 - 208
[6] ASYMMETRIC-SYNTHESIS VIA CHIRAL SULFUR-CONTAINING FERROCENES
HUA, DH
LAGNEAU, N
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 185 - ORGN
[7] Sulfur-containing chiral bis(oxazolines) tested in copper-catalyzed asymmetric cyclopropanation
Gao, MZ
Wang, B
Kong, DY
Zingaro, RA
Clearfield, A
Xu, ZL
[J]. SYNTHETIC COMMUNICATIONS, 2005, 35 (20) : 2665 - 2673
[8] REACTIONS OF SULFUR-CONTAINING PHOSPHONIUM SALTS
MUKAIYAMA, T
UEKI, M
[J]. TETRAHEDRON LETTERS, 1967, (35) : 3429 - +
[9] Novel and efficient synthesis of sulfur-containing heterocycles using a hypervalent iodine(III) reagent
Kita, Y
Egi, M
Ohtsubo, M
Saiki, T
Takada, T
Tohma, H
[J]. CHEMICAL COMMUNICATIONS, 1996, (19) : 2225 - 2226
[10] SYNTHESIS OF SULFUR-CONTAINING CHIRAL BOLA AMPHIPHILES
HAAS, HJ
ROTH, HJ
[J]. ARCHIV DER PHARMAZIE, 1987, 320 (09) : 958 - 958

← 1 2 3 4 5 →