A general procedure for a one-pot oxidative cleavage/Wittig reaction of glycols

被引：17

作者：

Dunlap, NK ^{[1
]}

Mergo, W ^{[1
]}

Jones, JM ^{[1
]}

Carrick, JD ^{[1
]}

机构：

[1] Middle Tennessee State Univ, Dept Chem, Murfreesboro, TN 37132 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 21期

关键词：

D O I：

10.1016/S0040-4039(02)00661-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative cleavage of a series of glycols using NaIO4 on silica gel in the presence of a series of stabilized ylides provides access to a number of synthetically useful alkenes. The case and general utility of this reaction is demonstrated here using several carbohydrates and amino acid derived glycols. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3923 / 3925

页数：3

共 16 条

[1] Dess-Martin periodinane oxidation of alcohols in the presence of stabilized phosphorus ylides: A convenient method for the homologation of alcohols via unstable aldehydes [J].

Barrett, AGM ;

Hamprecht, D ;

Ohkubo, M .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9376-9378

[2] Stereochemical elucidation of the pentacyclopropane antifungal agent FR-900848 [J].

Barrett, AGM ;

Doubleday, WW ;

Kasdorf, K ;

Tustin, GJ .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (10) :3280-3288

[3]

Crich D, 1999, SYNLETT, P67

[4] TOTAL SYNTHESIS OF TETRONOMYCIN [J].

HORI, K ;

HIKAGE, N ;

INAGAKI, A ;

MORI, S ;

NOMURA, K ;

YOSHII, E .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2888-2902

[5] APPLICATION OF THE SWERN OXIDATION TO THE MANIPULATION OF HIGHLY REACTIVE CARBONYL-COMPOUNDS [J].

IRELAND, RE ;

NORBECK, DW .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (12) :2198-2200

[6] STEREOSELECTIVE SYNTHESIS OF METHYL (1R) TRANS-HEMICARONALDEHYDES AND (1R) CIS-HEMICARONALDEHYDES FROM NATURAL TARTARIC ACID - APPLICATION TO THE SYNTHESIS OF S-BIOALLETHRIN AND DELTAMETHRIN INSECTICIDES [J].

KRIEF, A ;

DUMONT, W ;

PASAU, P ;

LECOMTE, P .

TETRAHEDRON, 1989, 45 (10) :3039-3052

[7]

Kumar KK, 1999, TETRAHEDRON, V55, P13899

[8] EFFICIENT PROCEDURES FOR INSITU TRAPPING OF (R)-GLYCERALDEHYDE AND (S)-GLYCERALDEHYDE ACETONIDES BY STABILIZED WITTIG REAGENTS [J].

LEONARD, J ;

MOHIALDIN, S ;

SWAIN, PA .

SYNTHETIC COMMUNICATIONS, 1989, 19 (20) :3529-3534

[9] One-pot oxidation and Wittig olefination of alcohols using O-iodoxybenzoic acid and stable Wittig ylide [J].

Maiti, A ;

Yadav, JS .

SYNTHETIC COMMUNICATIONS, 2001, 31 (10) :1499-1506

[10] Intermolecular Michael addition of substituted amines to a sugar-derived α,β-unsaturated ester:: Synthesis of 1-deoxy-D-gluco- and -L-ido-homonojirimycin, 1-deoxy-castanospermine and 1-deoxy-8a-epi-castanospermine [J].

Patil, NT ;

Tilekar, JN ;

Dhavale, DD .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (04) :1065-1074

← 1 2 →