Further Studies on the [1,2]-Wittig Rearrangement of 2-(2-Benzyloxy)aryloxazolines

被引：5

作者：

Aitken, R. Alan ^{[1
]}

Harper, Andrew D. ^{[1
]}

Inwood, Ryan A. ^{[1
]}

机构：

[1] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland

来源：

MOLECULES | 2022年 / 27卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

oxazoline; Wittig rearrangement; phthalide; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; SYNTHETIC UTILITY; AMINO-ACIDS; CYCLIZATION; OXAZOLINES; PHTHALIDES; GLYCOSIDES; COMPLEXES; CHEMISTRY;

D O I：

10.3390/molecules27103186

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The behaviour of 14 ortho-functionalised 2-aryloxazolines (11 of them prepared and characterised for the first time) with butyllithium has been examined. Significant limitations to the Wittig rearrangement of such systems are revealed. In terms of asymmetric Wittig rearrangement, good diastereoselectivity is obtained with a valine-derived 4-isopropyl oxazoline, but this is compromised by racemisation upon hydrolysis. More encouraging selectivity is achieved in the Wittig rearrangement of an acyclic phenylalanine-derived ortho-benzyloxy benzamide.

引用

页数：23

共 47 条

[1] Access to Diarylmethanols by Wittig Rearrangement ofortho-,meta-, andpara-Benzyloxy-N-Butylbenzamides [J].

Aitken, R. Alan ;

Harper, Andrew D. ;

Inwood, Ryan A. ;

Slawin, Alexandra M. Z. .

JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (07) :4692-4701

[2] Rationalisation of Patterns of Competing Reactivity by X-ray Structure Determination: Reaction of Isomeric (Benzyloxythienyl)oxazolines with a Base [J].

Aitken, R. Alan ;

Harper, Andrew D. ;

Slawin, Alexandra M. Z. .

MOLECULES, 2021, 26 (24)

[3] Base-Induced Cyclisation of ortho -Substituted 2-Phenyloxazolines to Give 3-Aminobenzofurans and Related Heterocycles [J].

Aitken, R. Alan ;

Harper, Andrew D. ;

Slawin, Alexandra M. Z. .

SYNLETT, 2017, 28 (14) :1738-1742

[4] ENANTIOMERICALLY PURE OXAZOLINES TETHERED TO ALCOHOLS - PREPARATION AND USE IN ASYMMETRIC CATALYSIS [J].

ALLEN, JV ;

WILLIAMS, JMJ .

TETRAHEDRON-ASYMMETRY, 1994, 5 (02) :277-282

[5] Adding the right (or left) twist to tris-chelate complexes - coordination chemistry of chiral oxazolylphenolates with M3+ ions (M = Al or lanthanide) [J].

Aspinall, Helen C. ;

Bacsa, John ;

Beckingham, Oliver D. ;

Eden, Edward G. B. ;

Greeves, Nicholas ;

Hobbs, Matthew D. ;

Potjewyd, Frances ;

Schmidtmann, Marc ;

Thomas, Christopher D. .

DALTON TRANSACTIONS, 2014, 43 (03) :1434-1442

[6] A mechanism for efficient proton-transfer catalysis. Intramolecular general acid catalysis of the hydrolysis of 1-arylethyl ethers of salicylic acid [J].

Barber, SE ;

Dean, KES ;

Kirby, AJ .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1999, 77 (5-6) :792-801

[7]

Bogoradovskii E.T., 1994, RUSS J GEN CHEM+, V64, P775

[8]

Cahiez G, 1999, SYNTHESIS-STUTTGART, P2138

[9] Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations [J].

Cariou, Claire A. M. ;

Kariuki, Benson M. ;

Snaith, John S. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (18) :3337-3348

[10] IMPROVEMENT IN THE ENANTIOSELECTIVITY OF THE HYDROGEN TRANSFER WITH NADH MODELS BEARING AMINO-ALCOHOLS AS CHIRAL AUXILIARIES [J].

CAZIN, J ;

DUFLOS, J ;

DUPAS, G ;

BOURGUIGNON, J ;

QUEGUINER, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (05) :867-872

← 1 2 3 4 5 →