INTERMOLECULAR AND INTRAMOLECULAR HETERO-DIELS-ALDER REACTIONS .43. THE 1ST EXAMPLE OF AN INCREASE IN THE ENANTIOSELECTIVITY OF A CHEMICAL-REACTION IN THE PRESENCE OF A CHIRAL LEWIS-ACID UNDER HIGH-PRESSURE

被引：43

作者：

TIETZE, LE ^{[1
]}

OTT, C ^{[1
]}

GERKE, K ^{[1
]}

BUBACK, M ^{[1
]}

机构：

[1] UNIV GOTTINGEN,INST PHYS CHEM,D-37077 GOTTINGEN,GERMANY

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1993年 / 32卷 / 10期

关键词：

D O I：

10.1002/anie.199314851

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselectivity increases from 4.5 to 20.4% ee in favor of the (–)‐enantiomer in the intramolecular hetero‐Diels‐Alder reaction of 1, which provides 2 and 3 when the pressure is increased from 1 to 5000 bar. A chiral Lewis acid is also employed in this reaction. (Figure Presented.) Copyright © 1993 by VCH Verlagsgesellschaft mbH, Germany

引用

页码：1485 / 1486

页数：2

共 40 条

[1] DIELS-ALDER REACTIONS OF CYCLOALKENONES .22. HIGH PRESSURE-LEWIS ACID-CATALYZED DIELS-ALDER REACTIONS OF 3-METHYLCYCLOHEX-2-EN-1-ONE - A STRAIGHTFORWARD ROUTE TO CIS AND TRANS ANGULARLY METHYLATED OCTALONES [J].

ABEN, RWM ;

MINUTI, L ;

SCHERREN, HW ;

TATICCHI, A .

TETRAHEDRON LETTERS, 1991, 32 (44) :6445-6448

[2] THE CHIRAL POOL AS A SOURCE OF ENANTIOSELECTIVE CATALYSTS AND AUXILIARIES [J].

BLASER, HU .

CHEMICAL REVIEWS, 1992, 92 (05) :935-952

[3] B-2'-ISOPRENYLDIISOPINOCAMPHEYLBORANE - AN EFFICIENT REAGENT FOR THE CHIRAL ISOPRENYLATION OF ALDEHYDES - A CONVENIENT ROUTE TO BOTH ENANTIOMERS OF IPSENOL AND IPSDIENOL [J].

BROWN, HC ;

RANDAD, RS .

TETRAHEDRON LETTERS, 1990, 31 (04) :455-458

[4] INTERMOLECULAR AND INTRAMOLECULAR HETERO DIELS-ALDER REACTIONS .26. DIASTEREOSELECTIVITY AND KINETICS OF INTERMOLECULAR HETERO DIELS-ALDER REACTIONS UNDER HIGH-PRESSURE - A SIGNIFICANT PRESSURE-INDUCED INCREASE IN STEREOSELECTIVITY [J].

BUBACK, M ;

TOST, W ;

HUBSCH, T ;

VOSS, E ;

TIETZE, LF .

CHEMISCHE BERICHTE, 1989, 122 (06) :1179-1186

[5] CHIRAL TITANIUM COMPLEXES FOR ENANTIOSELECTIVE ADDITION OF NUCLEOPHILES TO CARBONYL GROUPS [J].

DUTHALER, RO ;

HAFNER, A .

CHEMICAL REVIEWS, 1992, 92 (05) :807-832

[6] A NEW GENERAL SYNTHETIC APPROACH TO DITERPENES - APPLICATION TO SYNTHESES OF (+/-)-TAXODIONE AND (+/-)-ROYLEANONE [J].

ENGLER, TA ;

SAMPATH, U ;

NAGANATHAN, S ;

VELDE, DV ;

TAKUSAGAWA, F ;

YOHANNES, D .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5712-5727

[7] ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTION CATALYZED BY CHIRAL ACYLOXYBORANE COMPLEX [J].

FURUTA, K ;

KANEMATSU, A ;

YAMAMOTO, H ;

TAKAOKA, S .

TETRAHEDRON LETTERS, 1989, 30 (51) :7231-7232

[8] PREPARATION OF ENANTIOMERICALLY PURE CHIRAL ALCOHOLS BY ASYMMETRIC ALKYLATION OF GLYCOLATES [J].

HELMCHEN, G ;

WIERZCHOWSKI, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (01) :60-61

[9]

Helmchen G., 1984, ANGEW CHEM, V96, P59

[10] THE ROLE OF HIGH-PRESSURE METHODS IN ORGANIC-CHEMISTRY [J].

ISAACS, NS .

TETRAHEDRON, 1991, 47 (40) :8463-8497

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