Rearrangement of unactivated N-alkyl-O-benzoyl hydroxamic acid derivatives with phosphazene bases

被引：13

作者：

Clark, AJ ^{[1
]}

Al-Faiyz, YSS

Patel, D

Broadhurst, MJ

机构：

[1] Univ Warwick, Dept Chem, Coventry CV4 7AL, W Midlands, England

[2] Roche Discovery Welwyn, Welwyn Garden City AL7 3AY, Herts, England

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(01)00062-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The phosphazene super bases BTPP 5, P-2-'Bu 6, and P-4-'Bu 7 mediate the rearrangement of unactivated N-alkyl-O-benzoyl hydroxamic acid derivatives 8, 11a-f, 13 and 16 to give 2-benzoyloxy amides 9, 12a-f, 14 and 17. The rate of reaction was found to be dependant upon the steric nature of the N-alkyl substituent. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2007 / 2009

页数：3

共 7 条

[1] Rearrangements of activated O-acyl hydroxamic acid derivatives. [J].

Al-Faiyz, YSS ;

Clark, AJ ;

Filik, RP ;

Peacock, JL ;

Thomas, GH .

TETRAHEDRON LETTERS, 1998, 39 (10) :1269-1272

[2]

[Anonymous], MODERN SYNTHETIC MET

[3] An amidyl radical cyclisation approach towards the synthesis of β-lactams [J].

Clark, AJ ;

Peacock, JL .

TETRAHEDRON LETTERS, 1998, 39 (10) :1265-1268

[4] Base catalysed rearrangement of N-alkyl-O-acyl hydroxamic acids:: synthesis of 2-acyloxyamides [J].

Clark, AJ ;

Al-Faiyz, YSS ;

Broadhurst, MJ ;

Patel, D ;

Peacock, JL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (07) :1117-1127

[5]

ENDO Y, 1994, SYNTHESIS-STUTTGART, P1096

[6] BASE-PROMOTED REACTION OF O-SULFONYLATED HYDROXAMIC ACIDS WITH NUCLEOPHILES - A NEW METHOD FOR THE SYNTHESIS OF ALPHA-SUBSTITUTED AMIDES [J].

HOFFMAN, RV ;

NAYYAR, NK ;

CHEN, WT .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21) :5700-5707

[7] Phosphazene bases and the anionic oxy-Cope rearrangement [J].

Mamdani, HT ;

Hartley, RC .

TETRAHEDRON LETTERS, 2000, 41 (05) :747-749

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