α-Acyloxynitroso dienophiles in [4+2] hetero Diels-Alder cycloadditions: mechanistic insights

被引：15

作者：

Calvet, Geraldine ^{[2
]}

Coote, Susannah C. ^{[2
]}

Blanchard, Nicolas ^{[1
]}

Kouklovsky, Cyrille ^{[2
]}

机构：

[1] Univ Haute Alsace, ENSCMU, CNRS, Lab Chim Organ Bioorgan & Macromol,FRE 3253, F-68093 Mulhouse, France

[2] Univ Paris 11, CNRS, Lab Chim Procedes & Substance Nat, ICMMO,UMR 8182, F-91405 Orsay, France

来源：

TETRAHEDRON | 2010年 / 66卷 / 16期

关键词：

LEAD-TETRAACETATE OXIDATION; ACYL-NITROSO COMPOUNDS; N-O BOND; ASYMMETRIC DIELS; HYDROXAMIC ACID; STEREOSELECTIVE CYCLOADDITIONS; CHLORONITROSO COMPOUNDS; ACYLNITROSO DIENOPHILES; REDUCTIVE CLEAVAGE; D-SERIES;

D O I：

10.1016/j.tet.2010.02.065

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a beta-oxygenated moiety led to a domino [4+2] cycloaddition/sigma(N-O) bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the sigma(N-O) bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：2969 / 2980

页数：12

共 160 条

[1] First total synthesis of the marine alkaloids (±)-fasicularin and (±)-lepadiformine based on stereocontrolled intramolecular acylnitroso-Diels-Alder reaction [J].

Abe, H ;

Aoyagi, S ;

Kibayashi, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (19) :4583-4592

[2] Discovery of Innovative Small Molecule Therapeutics [J].

Abou-Gharbia, Magid .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (01) :2-9

[3] Generation of acylnitroso dienophiles: A study of metal catalysis [J].

Adamo, Mauro F. A. ;

Bruschi, Simone .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) :2666-2669

[4] Synthesis of enantiopure functionalized β-alkoxy γ-amino aldehydes by a new internal redox ring cleavage of carbohydrate-derived 1,2-oxazines [J].

Al-Harrasi, A ;

Reissig, HU .

SYNLETT, 2005, (07) :1152-1154

[5] USEFUL SYNTHESIS OF 3-OXODIHYDROISOINDOLES [J].

ANDERSON, PS ;

CHRISTY, ME ;

COLTON, CD ;

SHEPARD, KL .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (19) :3719-3723

[6]

[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650

[7] Asymmetric total synthesis of (-)-epibatidine [J].

Aoyagi, S ;

Tanaka, R ;

Naruse, M ;

Kibayashi, C .

TETRAHEDRON LETTERS, 1998, 39 (25) :4513-4516

[8] Synthesis of an 1-azaglucose analogue with ring-oxygen retained. [J].

Bach, P ;

Bols, M .

TETRAHEDRON LETTERS, 1999, 40 (17) :3461-3464

[9] SYNTHESIS OF D-BIOTIN FROM L-CYSTINE VIA INTRAMOLECULAR [3+2] CYCLOADDITION [J].

BAGGIOLINI, EG ;

LEE, HL ;

PIZZOLATO, G ;

USKOKOVIC, MR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (23) :6460-6462

[10]

Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677

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