Thermodynamically controlled cyclisation reactions with double phenylsulfanyl migration

被引：11

作者：

Carlisle, J ^{[1
]}

Fox, DJ ^{[1
]}

Warren, S ^{[1
]}

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

来源：

CHEMICAL COMMUNICATIONS | 2003年 / 21期

关键词：

D O I：

10.1039/b308609g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enantiomerically enriched C-2-symmetric tetrols were synthesised by a route involving a 'self-metathesis' reaction with Grubbs' second-generation ruthenium catalyst; these tetrols produced interesting bicyclic products when rearranged under acidic conditions.

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页码：2696 / 2697

页数：2

相关论文

共 13 条

[1] Asymmetric synthesis of tetrahydrofurans by competitive [1,2]-phenylsulfanyl (PhS) migrations under thermodynamic control [J].

Caggiano, L ;

Fox, DJ ;

House, D ;

Jones, ZA ;

Kerr, F ;

Warren, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (23) :2634-2645

[2] 1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].

CHEN, KM ;

HARDTMANN, GE ;

PRASAD, K ;

REPIC, O ;

SHAPIRO, MJ .

TETRAHEDRON LETTERS, 1987, 28 (02) :155-158

[3] DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].

EVANS, DA ;

CHAPMAN, KT ;

CARREIRA, EM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578

[4]

Fox DJ, 2002, ANGEW CHEM INT EDIT, V41, P2462, DOI 10.1002/1521-3773(20020715)41:14<2462::AID-ANIE2462>3.0.CO

[5]

2-3

[6] Desymmetrization of a centrosymmetric diepoxide: Efficient synthesis of a key intermediate in a total synthesis of hemibrevetoxin B [J].

Holland, JM ;

Lewis, M ;

Nelson, A .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (03) :747-753

[7]

Holland JM, 2001, ANGEW CHEM INT EDIT, V40, P4082, DOI 10.1002/1521-3773(20011105)40:21<4082::AID-ANIE4082>3.0.CO

[8]

2-T

[9] CATALYTIC ASYMMETRIC DIHYDROXYLATION [J].

KOLB, HC ;

VANNIEUWENHZE, MS ;

SHARPLESS, KB .

CHEMICAL REVIEWS, 1994, 94 (08) :2483-2547

[10] Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands [J].

Scholl, M ;

Ding, S ;

Lee, CW ;

Grubbs, RH .

ORGANIC LETTERS, 1999, 1 (06) :953-956