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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收藏

页码：3471 / 3474

页数：4

相关论文

共 18 条

[11] Facial selective photoreduction of steroids: Role of zeolites [J].

Rao, VJ ;

Uppili, SR ;

Corbin, DR ;

Schwarz, S ;

Lustig, SR ;

Ramamurthy, V .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (10) :2480-2481

[12] Mechanism of ene reactions of singlet oxygen. A two-step no-intermediate mechanism [J].

Singleton, DA ;

Hang, C ;

Szymanski, MJ ;

Meyer, MP ;

Leach, AG ;

Kuwata, KT ;

Chen, JS ;

Greer, A ;

Foote, CS ;

Houk, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1319-1328

[13] Asymmetric photoreactions within zeolites: Role of confinement and alkali metal ions [J].

Sivaguru, J ;

Natarajan, A ;

Kaanumalle, LS ;

Shailaja, J ;

Uppili, S ;

Joy, A ;

Ramamurthy, V .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (07) :509-521

[14] Ene hydroperoxidation of isobutenylarenes within dye-exchanged zeolite Na-Y: Control of site selectivity by cation-arene interactions [J].

Stratakis, M ;

Rabalakos, C ;

Mpourmpakis, G ;

Froudakis, GE .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07) :2839-2843

[15] Thionin-sensitized intrazeolite photooxygenation of trisubstituted alkenes: Substituent effects on the regioselectivity as probed through isotopic labeling [J].

Stratakis, M ;

Nencka, R ;

Rabalakos, C ;

Adam, W ;

Krebs, O .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8758-8763

[16] Intrazeolite photo-oxygenation of (R)-(-)-α-phellandrene [J].

Stratakis, M ;

Sofikiti, N .

JOURNAL OF CHEMICAL RESEARCH, 2002, (08) :374-375

[17] Regioselectivity in the ene reaction of singlet oxygen with alkenes [J].

Stratakis, M ;

Orfanopoulos, M .

TETRAHEDRON, 2000, 56 (12) :1595-1615

[18] Enhanced diastereoselectivity of an ene hydroperoxidation reaction by confinement within zeolite Na-Y; a stereoisotopic study [J].

Stratakis, M ;

Kosmas, G .

TETRAHEDRON LETTERS, 2001, 42 (34) :6007-6009