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

收藏

页码：10660 / 10675

页数：16

相关论文

共 131 条

[81]

MATSUMOTO M, 1977, TETRAHEDRON LETT, P3361

[82] Interpretation of the atmospheric oxygen bands, electronic levels of the oxygen molecule [J].

Mulliken, RS .

NATURE, 1928, 122 :505-505

[83] SINGLET OXYGEN IN OZONE CHEMISTRY [J].

MURRAY, RW ;

LIN, JWP ;

KAPLAN, ML .

ANNALS OF THE NEW YORK ACADEMY OF SCIENCES, 1970, 171 (01) :121-&

[84] REGIOSELECTIVE REACTION OF SINGLET OXYGEN WITH CIS-ALKENES [J].

ORFANOPOULOS, M ;

STRATAKIS, M ;

ELEMES, Y .

TETRAHEDRON LETTERS, 1989, 30 (36) :4875-4878

[85] SOLVENT EFFECTS ON THE SIDE SELECTIVITY OF SINGLET OXYGEN WITH ALPHA, BETA-UNSATURATED ESTERS - NEW EVIDENCE FOR A PEREPOXIDE INTERMEDIATE [J].

ORFANOPOULOS, M ;

STRATAKIS, M .

TETRAHEDRON LETTERS, 1991, 32 (49) :7321-7324

[86] STEREOCHEMISTRY OF THE SINGLET OXYGEN OLEFIN-ENE REACTION [J].

ORFANOPOULOS, M ;

STEPHENSON, LM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (04) :1417-1418

[87] REGIOSELECTIVE REACTION OF SINGLET OXYGEN WITH ALPHA,BETA-UNSATURATED ESTERS [J].

ORFANOPOULOS, M ;

FOOTE, CS .

TETRAHEDRON LETTERS, 1985, 26 (48) :5991-5994

[88] SITE SPECIFICITY IN THE SINGLET OXYGEN - TRISUBSTITUTED OLEFIN REACTION [J].

ORFANOPOULOS, M ;

GRDINA, SMB ;

STEPHENSON, LM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (01) :275-276

[89] GEMINAL SELECTIVITY OF SINGLET OXYGEN ENE REACTIONS - THE NONBONDING LARGE GROUP EFFECT [J].

ORFANOPOULOS, M ;

STRATAKIS, M ;

ELEMES, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6417-6419

[90] DO ROTATIONAL BARRIERS DICTATE THE REGIOSELECTIVITY IN THE ENE REACTIONS OF SINGLET OXYGEN AND TRIAZOLINEDIONE WITH ALKENES [J].

ORFANOPOULOS, M ;

STRATAKIS, M ;

ELEMES, Y ;

JENSEN, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (08) :3180-3181

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