Novel concepts in directed biaryl synthesis, part 94 -: Atropo-enantioselective ring cleavage of Lewis acid modified biaryl thionolactones

被引：7

作者：

Bringmann, G

Wuzik, A

Kümmel, J

Schenk, WA

机构：

[1] Univ Wurzburg, Inst Chim Organ, D-97074 Wurzburg, Germany

[2] Univ Wurzburg, Inst Anorgan Chem, D-97074 Wurzburg, Germany

来源：

ORGANOMETALLICS | 2001年 / 20卷 / 08期

关键词：

D O I：

10.1021/om001040e

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Attachment of an achiral, ruthenium-based Lewis acid fragment to configurationally unstable biaryl thionolactones la-lc, atropo-enantioselective reductive lactone cleavage of the resulting complexes with chiral hydride reagents, and subsequent decomplexation leads to axially chiral thioethers 3a-3c with enantiomeric ratios of up to 92:8.

引用

页码：1692 / 1694

页数：3

共 33 条

[1] [Anonymous], 1994, Angew. Chem
[2] [Anonymous], ANGEW CHEM
[3] First atropo-divergent total synthesis of the antimalarial korupensamines A and B by the "lactone method"
Bringmann, G
Ochse, M
Götz, R
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (07) : 2069 - 2077
[4] Nondynamic and dynamic kinetic resolution of lactones with stereogenic centers and axes: Stereoselective total synthesis of herbertenediol and mastigophorenes A and B
Bringmann, G
Pabst, T
Henschel, P
Kraus, J
Peters, K
Peters, EM
Rycroft, DS
Connolly, JD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) : 9127 - 9133
[5] SYNTHESIS AND RING-OPENING REACTIONS OF CATIONIC RUTHENIUM BIARYL THIONOLACTONE COMPLEXES
BRINGMANN, G
SCHONER, B
SCHUPP, O
SCHENK, WA
REUTHER, I
PETERS, K
PETERS, EM
VONSCHNERING, HG
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 472 (1-2) : 275 - 284
[6] Enantioselective addition of diethylzinc to aldehydes using novel axially chiral 2-aminomethyl-1-(2′-hydroxyphenyl)naphthalene catalysts
Bringmann, G
Breuning, M
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (04) : 667 - 679
[7] Novel concepts in directed biaryl synthesis - Part 77 - Atropo-enantioselective reduction of configurationally unstable biaryl lactones with BINAL-H
Bringmann, G
Breuning, M
[J]. TETRAHEDRON-ASYMMETRY, 1999, 10 (02) : 385 - 390
[8] NOVEL CONCEPTS IN DIRECTED BIARYL SYNTHESIS .12. 1ST ATROPO-ENANTIOSELECTIVE RING-OPENING OF ACHIRAL BIARYLS CONTAINING LACTONE BRIDGES WITH CHIRAL HYDRIDE-TRANSFER REAGENTS DERIVED FROM BORANE
BRINGMANN, G
HARTUNG, T
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (06): : 761 - 762
[9] Novel concepts in directed biaryl synthesis, part 78. The lactone concept: An efficient pathway to axially chiral natural products and useful reagents
Bringmann, G
Breuning, M
Tasler, S
[J]. SYNTHESIS-STUTTGART, 1999, (04): : 525 - 558
[10] BRINGMANN G, 2001, IN PRESS PROG CHEM O

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