Enantioselective Diels-Alder Reactions with Anomalous endo/exo Selectivities Using Conformationally Flexible Chiral Supramolecular Catalysts

Swapped selectivities: The use of tailor‐made catalysts results in anomalous endo/exo selectivities and high enantioselectivities in the Diels–Alder reactions of cyclopentadiene with different acroleins (see scheme). These supramolecular catalysts are prepared in situ from chiral diols, arylboronic...

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Bibliographic Details
Published in:	Angewandte Chemie International Edition Vol. 50; no. 51; pp. 12189 - 12192
Main Authors:	Hatano, Manabu, Mizuno, Tomokazu, Izumiseki, Atsuto, Usami, Ryota, Asai, Takafumi, Akakura, Matsujiro, Ishihara, Kazuaki
Format:	Journal Article
Language:	English
Published:	Weinheim WILEY-VCH Verlag 16-12-2011 WILEY‐VCH Verlag Wiley Subscription Services, Inc
Edition:	International ed. in English
Subjects:	Acroleins asymmetric catalysis Catalysis Catalysts cycloaddition Cyclopentadiene Diels-Alder reactions Dienes Diols Selectivity supramolecular catalysis
Online Access:	Get full text
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Summary:	Swapped selectivities: The use of tailor‐made catalysts results in anomalous endo/exo selectivities and high enantioselectivities in the Diels–Alder reactions of cyclopentadiene with different acroleins (see scheme). These supramolecular catalysts are prepared in situ from chiral diols, arylboronic acid, and tris(pentafluorophenyl)borane, and can discriminate the re/si face of the dienophile as well as the endo/exo approach of the diene.
Bibliography:	MEXT Yazaki Memorial Foundation for Science and Technology Financial support for this project was partially provided by MEXT, KAKENHI (21750094, 21200033), the Global COE Program of MEXT, and Yazaki Memorial Foundation for Science and Technology. We are grateful to the Tosoh Finechem Corporation and Central Glass Co., Ltd. for providing organometallic reagents. KAKENHI - No. 21750094; No. 21200033 ark:/67375/WNG-02MJ3LF2-T istex:949438F9DEC716E91AEA89529F34F5184B613E1F ArticleID:ANIE201106497 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201106497