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Exploration of the new horizon of Di...

Huang, Yong.

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Exploration of the new horizon of Diels-Alder reactions: Asymmetric catalysis.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Exploration of the new horizon of Diels-Alder reactions: Asymmetric catalysis./
Author:	Huang, Yong.
Description:	433 p.
Notes:	Source: Dissertation Abstracts International, Volume: 63-07, Section: B, page: 3299.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3060222
ISBN:	0493758119

Exploration of the new horizon of Diels-Alder reactions: Asymmetric catalysis.
Huang, Yong.

Exploration of the new horizon of Diels-Alder reactions: Asymmetric catalysis. - 433 p.

Source: Dissertation Abstracts International, Volume: 63-07, Section: B, page: 3299.

Thesis (Ph.D.)--The University of Chicago, 2002.

The first chapter of this thesis describes a highly enantioselective DA reaction catalyzed by a salen-Cr(III) complex. A very board range of dienes, including 1-amino-3-siloxybutadienes and 1-aminobutadienes has been affected by this catalyst. The reaction proceeds in high yield, with complete <italic> endo</italic> selectivity and up to >97% ee. This methodology provides a very powerful asymmetric process for synthesis of six-membered carbon cycles containing a quaternary stereogenic center. The reaction can be easily performed in large scale, allowing gram-scale total syntheses of (+)-tabersonine and (+)-16-methoxytabersonine.

ISBN: 0493758119

Exploration of the new horizon of Diels-Alder reactions: Asymmetric catalysis.
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020 $a 0493758119
035 $a (UnM)AAI3060222
035 $a AAI3060222
040 $a UnM $c UnM
100 1 $a Huang, Yong. $3 1257160
245 1 0 $a Exploration of the new horizon of Diels-Alder reactions: Asymmetric catalysis.
300 $a 433 p.
500 $a Source: Dissertation Abstracts International, Volume: 63-07, Section: B, page: 3299.
500 $a Adviser: Viresh H. Rawal.
502 $a Thesis (Ph.D.)--The University of Chicago, 2002.
520 $a The first chapter of this thesis describes a highly enantioselective DA reaction catalyzed by a salen-Cr(III) complex. A very board range of dienes, including 1-amino-3-siloxybutadienes and 1-aminobutadienes has been affected by this catalyst. The reaction proceeds in high yield, with complete <italic> endo</italic> selectivity and up to >97% ee. This methodology provides a very powerful asymmetric process for synthesis of six-membered carbon cycles containing a quaternary stereogenic center. The reaction can be easily performed in large scale, allowing gram-scale total syntheses of (+)-tabersonine and (+)-16-methoxytabersonine.
520 $a The second chapter discusses the 2<super>nd</super> generation silylsalen-Co(III) catalysts for enantioselective DA reactions of aminobutadienes, as inspired by a systematic survey of catalytic activities of metal-salen complexes and an X-ray structure of a salen-cobalt-benzaldehyde complex. These newly synthesized complexes are the most effective catalysts for the asymmetric DA reaction, achieving the world-record high substrate/catalyst ratio. Detailed discussion also includes some unique features of these silysalen-cobalt complexes that greatly expand the scope of this DA reaction: these catalysts can response to the changes of functional groups and “intelligently” adopt the desired coordination conformation. Application of this methodology has been demonstrated by the total synthesis of (γ)-(−)-lycorane
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3060222