Remarkable change of the diastereoselection in the dye-sensitized ene hydroperoxidation of chiral alkenes by zeolite confinement

被引：23

作者：

Stratakis, M ^{[1
]}

Kalaitzakis, D ^{[1
]}

Stavroulakis, D ^{[1
]}

Kosmas, G ^{[1
]}

Tsangarakis, C ^{[1
]}

机构：

[1] Univ Crete, Dept Chem, GR-71409 Iraklion, Greece

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 19期

关键词：

D O I：

10.1021/ol0352660

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The ene reaction of singlet oxygen with chiral trisubstituted alkenes bearing an alkyl and a phenyl group at the stereogenic center is erythro diastereoselective in solution and threo diastereoselective if carried out within zeolite Na-Y. The change of the diastereoselection trend by zeolite confinement is attributed to a synergism of steric effects and cation-pi interactions.

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页码：3471 / 3474

页数：4

相关论文

共 18 条

[1]

ADAM W, 1990, LIEBIGS ANN CHEM, P1051

[2] Diastereoselective singlet oxygen ene reaction (Schenck reaction) and diastereoselective epoxidations of heteroatom-substituted acyclic chiral olefins: A mechanistic comparison [J].

Adam, W ;

Brunker, HG ;

Kumar, AS ;

Peters, EM ;

Peters, K ;

Schneider, U ;

vonSchnering, HG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (08) :1899-1905

[3] Photochemical reactions in the interior of a zeolite. Part 5: The origin of the zeolite induced regioselectivity in the singlet oxygen ene reaction [J].

Clennan, EL ;

Sram, JP .

TETRAHEDRON, 2000, 56 (36) :6945-6950

[4] A complete basis set estimate of cation-π bond strengths:: Na+(ethylene) and Na+(benzene) [J].

Feller, D .

CHEMICAL PHYSICS LETTERS, 2000, 322 (06) :543-548

[5] Cation controlled singlet oxygen mediated oxidation of olefins within zeolites [J].

Kaanumalle, LS ;

Shailaja, J ;

Robbins, RJ ;

Ramamurthy, V .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2002, 153 (1-3) :55-65

[6] ASYMMETRIC INDUCTION . A MODEL FOR ADDITIONS TO CARBONYLS DIRECTLY BONDED TO ASYMMETRIC CARBONS [J].

KARABATS.GJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (06) :1367-&

[7]

KROPF H, 1987, J CHEM RES-S, P412

[8] A new experimental protocol for intrazeolite photooxidations. The first product-based estimate of an upper limit for the intrazeolite singlet oxygen lifetime [J].

Pace, A ;

Clennan, EL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11236-11237

[9]

PREIN M, 1996, ANGEW CHEM INT EDIT, V35, P519

[10] Energy transfer, proton transfer and electron transfer reactions within zeolites [J].

Ramamurthy, V ;

Lakshminarasimhan, P ;

Grey, CP ;

Johnston, LJ .

CHEMICAL COMMUNICATIONS, 1998, (22) :2411-2424