Chirality transfer from a biphenyl axis to a spiro centre and its reverse: sequential self-immolation

被引：8

作者：

Baker, RW

Kyasnoor, RV

Sargent, MV ^{[1
]}

机构：

[1] Univ Western Australia, Dept Chem, Nedlands, WA 6907, Australia

[2] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 17期

关键词：

D O I：

10.1016/S0040-4039(99)00427-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Schmidt reaction of (S)-1-(2,'4',6-trimethoxy-4,6'-dimethylbiphenyl-2-yl)ethanone 8 furnished the expected amide 9 (43%) accompanied by (S)-2,7'-dimethoxy-3',5',6-trimethylspiro[cyclohexa-2,5-diene-1,1'-(1H)isoindole]-4-one 12 (30%) which on reduction with zinc and acetic acid and subsequent methylation regenerated ketone 8. (C) 1999 Elsevier Science Ltd. All rights reserved.

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页码：3475 / 3478

页数：4

相关论文

共 15 条

[1] THE STRUCTURE OF PHENYLDIHYDROTHEBAINE [J].

BENTLEY, KW ;

ROBINSON, R .

JOURNAL OF THE CHEMICAL SOCIETY, 1952, (MAR) :947-957

[2] CONSTITUENTS OF EUPOMATIA SPECIES .11. NEW EUPODIENONE LIGNANS FROM THE FLOWERS OF EUPOMATIA-LAURINA [J].

CARROLL, AR ;

TAYLOR, WC .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1990, 43 (11) :1871-1879

[3] NEW PROAPORPHINE ALKALOIDS FROM ROEMERIA-HYBRIDA [J].

GOZLER, B ;

GOZLER, T ;

METE, IE ;

FREYER, AJ ;

GUINAUDEAU, H ;

SHAMMA, M .

TETRAHEDRON, 1987, 43 (08) :1765-1770

[4] STERIC EFFECTS OF METHOXY-GROUPS IN SOME BIOPHENYLS DERIVED FROM THEBAINE .1. UNBRIDGED BIPHENYLS [J].

HALL, DM ;

MANSER, WWT .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (02) :323-&

[5] TERPENOIDS .13. STEREOCHEMISTRY OF CHAPARRIN CHAPARROL AND RELATED COMPOUNDS [J].

HOLLANDS, TR ;

DEMAYO, P ;

NISBET, M ;

CRABBE, P .

CANADIAN JOURNAL OF CHEMISTRY, 1965, 43 (11) :3008-&

[6] A formal synthesis of both atropenantiomers of desertorin C [J].

Kyasnoor, RV ;

Sargent, MV .

CHEMICAL COMMUNICATIONS, 1998, (24) :2713-2714

[7] COMPLETE INTRAMOLECULAR TRANSFER OF A CENTRAL CHIRAL ELEMENT TO AN AXIAL CHIRAL ELEMENT - OXIDATION OF (S)-4-NAPHTHYLDIHYDROQUINOLINES TO (S)-4-NAPHTHYLQUINOLINES [J].

MEYERS, AI ;

WETTLAUFER, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (04) :1135-1136

[8]

Mislow K., 1966, INTRO STEREOCHEMISTR

[9] OXAZOLINE-MEDIATED BIARYL COUPLING REACTIONS - STEREOCONTROLLED SYNTHESIS OF 2,2',6,6'-TETRASUBSTITUTED BIPHENYLS [J].

MOORLAG, H ;

MEYERS, AI .

TETRAHEDRON LETTERS, 1993, 34 (44) :6989-6992

[10] A NEW SYNTHESIS OF ANTHRAQUINONES USING DIHYDRO-OXAZOLES AND GRIGNARD-REAGENTS DERIVED FROM MG(ANTHRACENE)(THF)3 [J].

NICOLETTI, TM ;

RASTON, CL ;

SARGENT, MV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01) :133-138