Stereospecific [2,3] sigmatropic rearrangement of allylic sulfoxides and selenoxides.: Synthesis of novel polycyclic allylic alcohols and α-hydroxy ketones

被引：23

作者：

Koprowski, M

Krawczyk, E

Skowroñska, A

McPartlin, M

Choi, N

Radojevic, S

机构：

[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Heteroorgan Chem, PL-90363 Lodz, Poland

[2] Univ N London, Fac Sci, Crystallog Lab, London N7 8QB, England

来源：

TETRAHEDRON | 2001年 / 57卷 / 06期

关键词：

rearrangements; cyclic ketones; cyclitols; phosphoric acid and derivatives;

D O I：

10.1016/S0040-4020(00)01083-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereospecific [2,3] sigmatropic rearrangement of functionalized bi- or tricyclic allylic sulfoxides and selenoxides as a route to new allylic alcohols and their transformation into the corresponding ol-hydroxy ketones having a defined stereochemistry is described. It has been demonstrated that cycloadducts, derived from [4+2] cycloaddition of (Z)-1-alkylthio-2-diethoxyphosphoryloxy-1,3-dienes to a various dienophiles, are versatile synthons carrying much structural and stereochemical information. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：1105 / 1118

页数：14

共 50 条

[1] STEREOSPECIFIC SYNTHESIS OF (+/-)-(E)-NUCIFEROL VIA [2,3]-SIGMATROPIC REARRANGEMENT OF ALLYLIC SULFOXIDES
GRIECO, PA
FINKELHO.RS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (12): : 2245 - 2247
[2] EFFICIENT STEREOCONTROL IN THE [2,3] SIGMATROPIC REARRANGEMENT OF ALLYLIC SULFOXIDES
SATO, T
OTERA, J
NOZAKI, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12): : 2779 - 2780
[3] ALLYLIC ALCOHOLS FORMATION BY OXIDATION OF ALLYLIC PHENYL TELLURIDES - A POSSIBLE [2,3]SIGMATROPIC REARRANGEMENT OF ALLYLIC TELLUROXIDES
UEMURA, S
FUKUZAWA, S
OHE, K
[J]. TETRAHEDRON LETTERS, 1985, 26 (07) : 921 - 924
[4] Trifluoromethyl Sulfoxides from Allylic Alcohols and Electrophilic SCF3 Donor by [2,3]-Sigmatropic Rearrangement
Maeno, Mayaka
Shibata, Norio
Cahard, Dominique
[J]. ORGANIC LETTERS, 2015, 17 (08) : 1990 - 1993
[5] Ab initio study of [2,3] sigmatropic rearrangement of allylic nitroxides and sulfoxides
Jursic, BS
[J]. JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 1995, 358 : 131 - 138
[6] ENANTIOSELECTIVE SYNTHESIS OF ALLYLIC ALCOHOLS VIA ASYMMETRIC [2,3]-SIGMATROPIC MEISENHEIMER REARRANGEMENT
ENDERS, D
KEMPEN, H
[J]. SYNLETT, 1994, (11) : 969 - 971
[7] From Allylic Sulfoxides to Allylic Sulfenates: Fifty Years of a Never-Ending [2,3]-Sigmatropic Rearrangement
Colomer, Ignacio
Velado, Marina
Fernandez de la Pradilla, Roberto
Viso, Alma
[J]. CHEMICAL REVIEWS, 2017, 117 (24) : 14201 - 14243
[8] [2,3] SIGMATROPIC REARRANGEMENT OF ALLYLIC NITROXIDES AND SULFOXIDES BY AB-INITIO METHODS
JURSIC, BS
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 : 118 - COMP
[9] Theoretical Studies of [2,3]-Sigmatropic Rearrangements of Allylic Selenoxides and Selenimides
Bayse, Craig A.
Antony, Sonia
[J]. MOLECULES, 2009, 14 (09) : 3229 - 3236
[10] OXIDATIVELY ASSISTED HYDROLYSIS OF ALLYLIC IODIDES TO REARRANGED ALLYLIC ALCOHOLS - A NEW EXAMPLE OF [2,3] SIGMATROPIC REARRANGEMENT
YAMAMOTO, S
ITANI, H
TSUJI, T
NAGATA, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) : 2908 - 2909

← 1 2 3 4 5 →