The first vanadium-catalyzed oxidation of aryl allylic selenides with in situ [2,3] sigmatropic rearrangement

被引：8

作者：

Carter, RG ^{[1
]}

Bourland, TC ^{[1
]}

机构：

[1] Univ Mississippi, Dept Chem & Biochem, Oxford, MS 38677 USA

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 20期

关键词：

D O I：

10.1039/b006278m

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The efficient synthesis of a series of 2 degrees allylic alcohols from a vanadium-catalyzed oxidation of suitably disposed allylic selenides with tandem [2,3] sigmatropic rearrangement is outlined.

引用

页码：2031 / 2032

页数：2

共 19 条

[1] THE OXIDATION OF EBSELEN METABOLITES TO THIOL OXIDANTS CATALYZED BY LIVER-MICROSOMES AND PERFUSED-RAT-LIVER [J].

AKERBOOM, TPM ;

SIES, H ;

ZIEGLER, DM .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1995, 316 (01) :220-226

[2]

[Anonymous], 1988, CHEM SULFONES SULFOX

[3]

Bolm C, 1995, ANGEW CHEM INT EDIT, V34, P2640

[4] Preparation of selenoxides from the catalytic autoxidation of organoselenides with nitrogen oxides [J].

Bosch, E ;

Kochi, JK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (22) :2731-2738

[5] LIVER MICROSOME AND FLAVIN-CONTAINING MONOOXYGENASE CATALYZED OXIDATION OF ORGANIC SELENIUM-COMPOUNDS [J].

CHEN, GP ;

ZIEGLER, DM .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1994, 312 (02) :566-572

[6] Catalytic asymmetric oxidation of tert-butyl disulfide.: Synthesis of tert-butanesulfinamides, tert-butyl sulfoxides, and tert-butanesulfinimines [J].

Cogan, DA ;

Liu, GC ;

Kim, KJ ;

Backes, BJ ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (32) :8011-8019

[7] ENANTIOPURE N-ACYLDIHYDROPYRIDONES AS SYNTHETIC INTERMEDIATES - THE FIRST ASYMMETRIC-SYNTHESIS OF TRANS-DECAHYDROQUINOLINE ALKALOID-(+)-219A [J].

COMINS, DL ;

DEHGHANI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :794-795

[8] ASYMMETRIC OXIDATION OF SIMPLE SELENIDES TO SELENOXIDES IN HIGH ENANTIOPURITY - STEREOCHEMICAL ASPECTS OF THE ALLYL SELENOXIDE ALLYL SELENENATE REARRANGEMENT [J].

DAVIS, FA ;

REDDY, RT .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) :2599-2606

[9]

Fujita K, 1998, SYNLETT, P987

[10] ASYMMETRIC [2,3] SIGMATROPIC REARRANGEMENT VIA CHIRAL SELENOXIDE WITH SHARPLESS OXIDANTS [J].

KOMATSU, N ;

NISHIBAYASHI, Y ;

UEMURA, S .

TETRAHEDRON LETTERS, 1993, 34 (14) :2339-2342

← 1 2 →