The nitroso ene reaction: A regioselective and stereoselective allylic nitrogen functionalization of mechanistic delight and synthetic potential

被引：255

作者：

Adam, W ^{[1
]}

Krebs, O ^{[1
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

来源：

CHEMICAL REVIEWS | 2003年 / 103卷 / 10期

关键词：

ALPHA-CHLORONITROSO COMPOUNDS; HYDROXY-GROUP DIRECTIVITY; SINGLET OXYGEN; ASYMMETRIC-SYNTHESIS; ACYLNITROSO COMPOUNDS; ALKALOID SYNTHESIS; BETA-LACTAMS; AMINO-ACIDS; IN-SITU; AMINATION;

D O I：

10.1021/cr030004x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The mechanistically challenging and synthetically promising nitroso ene reaction was investigated. A variety of aspects on mechanism and selectivity as well as synthetic applications and catalytic variations of the nitroso ene reaction were presented. It was found that acyl-nitroso compounds are the most reactive nitroso enophiles and also well-known to engage in cycloaddition.

引用

页码：4131 / 4146

页数：16

共 134 条

[1] Abele S, 2000, EUR J ORG CHEM, V2000, P1
[2] ADDITION OF ARYL NITRENES TO OLEFINS
ABRAMOVITCH, RA
CHALLAND, SR
YAMADA, Y
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (11) : 1541 - 1547
[3] Hydroxy-group directivity in the nitroso ene reaction: Diastereo- and regioselective amination of chiral allylic alcohols
Adam, W
Bottke, N
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (40) : 9846 - 9847
[4] CYCLOADDITION OF NITROSOBENZENE TO A TRIMETHYLENEMETHANE DIRADICAL - THE 1ST CASE OF ISOXAZOLINE FORMATION FROM INSITU GENERATED NITROXIDES THROUGH SPIN TRAPPING
ADAM, W
BOTTLE, SE
PETERS, K
[J]. TETRAHEDRON LETTERS, 1991, 32 (34) : 4283 - 4286
[5] Intramolecular and intermolecular kinetic isotope effects (KIE) in the nitrosoarene ene reaction: Experimental evidence for reversible intermediate formation
Adam, W
Krebs, O
Orfanopoulos, M
Stratakis, M
Vougioukalakis, GC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) : 2420 - 2425
[6] Efficient π-facial control in the ene reaction of nitrosoarene, triazolinedione, and singlet oxygen with tiglic amides of the bornane-derived sultam as chiral auxiliary:: An economical synthesis of enantiomerically pure nitrogen- and oxygen-functionalized acrylic acid derivatives
Adam, W
Degen, HG
Krebs, O
Saha-Möller, CR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) : 12938 - 12939
[7] Ene reaction of singlet oxygen, triazolinedione, and nitrosoarene with chiral deuterium-labeled allylic alcohols: The interdependence of diastereoselectivity and regioselectivity discloses mechanistic insights into the hydroxy-group directivity
Adam, W
Bottke, N
Krebs, O
Lykakis, I
Orfanopoulos, M
Stratakis, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (48) : 14403 - 14409
[8] Control of regioselectivity by the lone substituent through steric and electronic effects in the nitrosoarene ene reaction of deuterium-labeled trisubstituted alkenes
Adam, W
Krebs, O
Orfanopoulos, M
Stratakis, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24) : 8395 - 8399
[9] An experimental and computational study on the reactivity and regioselectivity for the nitrosoarene ene reaction: Comparison with triazolinedione and singlet oxygen
Adam, W
Bottke, N
Engels, B
Krebs, O
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (23) : 5542 - 5548
[10] Steric and conformational control of the regioselectivities in the ene reaction with trisubstituted cycloalkenes: Comparison of the enophiles singlet oxygen, triazolinedione, and nitrosoarene
Adam, W
Bottke, N
Krebs, O
[J]. ORGANIC LETTERS, 2000, 2 (21) : 3293 - 3296

← 1 2 3 4 5 6 7 8 9 10 →