Stereoelectronic and solvent effects on the allylic oxyfunctionalization of alkenes with singlet oxygen

被引：30

作者：

Alberti, Mariza N. ^{[1
]}

Orfanopoulos, Michael ^{[1
]}

机构：

[1] Univ Crete, Dept Chem, Iraklion 71003, Greece

来源：

TETRAHEDRON | 2006年 / 62卷 / 46期

关键词：

singlet oxygen; ene reactions; stereoselectivity; electronic effects; solvent effects;

D O I：

10.1016/j.tet.2006.07.106

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The factors that control the stereochemistry of sensitized photooxygenation of alkenes via singlet oxygen (ene reaction) are selectively reported. We also introduce our most recent stereoelectronic effects on the singlet oxygen-ene reaction. The origin of site selectivity and solvent-dependent stereoselectivity in this classical ene reaction with simple as well as functionalized alkenes is highlighted. These studies and other similar studies have enhanced substantially the utility of singlet oxygen in the synthesis of natural and non-natural products. (c) 2006 Published by Elsevier Ltd.

引用

页码：10660 / 10675

页数：16

共 131 条

[1] MECHANISMS OF PHOTODEGRADATION OF POLY(3-ALKYLTHIOPHENES) IN SOLUTION
ABDOU, MSA
HOLDCROFT, S
[J]. MACROMOLECULES, 1993, 26 (11) : 2954 - 2962
[2] ADAM W, 1986, SYNTHESIS-STUTTGART, P1050
[3] DIASTEREOSELECTIVE ENE REACTION IN THE PHOTOOXYGENATION OF THE SILYL CYANOHYDRINS OF ALPHA,BETA-UNSATURATED ALDEHYDES - NECESSITY FOR A COMMON SYMMETRICAL INTERMEDIATE OF THE PEREPOXIDE TYPE
ADAM, W
CATALANI, LH
GRIESBECK, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (26) : 5494 - 5496
[4] SYNTHESIS OF THE 1ST ALPHA-METHYLENE-BETA-PEROXYLACTONE - REGIOSPECIFIC ENE REACTION OF O-1(2) WITH ALPHA,BETA-UNSATURATED CARBOXYLIC-ACIDS
ADAM, W
GRIESBECK, A
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (12): : 1070 - 1071
[5] BETA-STANNYL ALLYLIC ALCOHOLS THROUGH PHOTOOXYGENATION (SCHENCK REACTION) OF VINYLSTANNANES AND REDUCTION OF THE RESULTING ALLYLIC HYDROPEROXIDES - SYNTHESIS AND SELECTED TRANSFORMATIONS
ADAM, W
KLUG, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) : 2695 - 2699
[6] HYDROXY-DIRECTED REGIOSELECTIVE AND DIASTEREOSELECTIVE ENE REACTION OF SINGLET OXYGEN WITH CHIRAL ALLYLIC ALCOHOLS
ADAM, W
NESTLER, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (12) : 5041 - 5049
[7] DIASTEREOSELECTIVE AND REGIOSELECTIVE PHOTOOXYGENATION OF A CHIRAL ALLYLIC AMINE AND ITS ACYL DERIVATIVES - STEREOCHEMICAL EVIDENCE FOR A STEERING EFFECT BY THE AMINO GROUP IN THE ENE REACTION OF SINGLET OXYGEN
ADAM, W
BRUNKER, HG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) : 3008 - 3009
[8] PHOTOOXYGENATION OF CHIRAL ALLYLIC ALCOHOLS - HYDROXY-DIRECTED REGIOSELECTIVE AND DIASTEREOSELECTIVE ENE REACTION OF SINGLET OXYGEN
ADAM, W
NESTLER, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) : 6549 - 6550
[9] Synthesis of 4,6-dideoxyfuranoses through the regioselective and diastereoselective oxyfunctionalization of a dimethylphenylsilyl-substituted chiral homoallylic alcohol
Adam, W
Saha-Möller, CR
Schmid, KS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22) : 7365 - 7371
[10] PHOTOOXYGENATION OF OLEFINS IN THE PRESENCE OF TITANIUM(IV) CATALYST - A CONVENIENT ONE-POT SYNTHESIS OF EPOXY ALCOHOLS
ADAM, W
BRAUN, M
GRIESBECK, A
LUCCHINI, V
STAAB, E
WILL, B
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (01) : 203 - 212

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