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The rational design of chiral alkyl ...

Solow, Michael Alan.

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The rational design of chiral alkyl dihaloboranes and their use as asymmetric Diels-Alder catalysts.

Record Type:	Electronic resources : Monograph/item
Title/Author:	The rational design of chiral alkyl dihaloboranes and their use as asymmetric Diels-Alder catalysts./
Author:	Solow, Michael Alan.
Description:	194 p.
Notes:	Source: Dissertation Abstracts International, Volume: 56-05, Section: B, page: 2638.
Contained By:	Dissertation Abstracts International56-05B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9529506

The rational design of chiral alkyl dihaloboranes and their use as asymmetric Diels-Alder catalysts.
Solow, Michael Alan.

The rational design of chiral alkyl dihaloboranes and their use as asymmetric Diels-Alder catalysts. - 194 p.

Source: Dissertation Abstracts International, Volume: 56-05, Section: B, page: 2638.

Thesis (Ph.D.)--University of California, Berkeley, 1994.

The Diels-Alder reaction, because of its highly ordered transition state and its ability to generate four stereocenters simultaneously, has become a testing ground for modern enantioselective catalysis. The rational design of a catalyst system can allow for variation and manipulation of attractive forces between catalyst and substrate which allow one to fine tune a catalyst system to be both active and stereoselective. This dissertation describes the synthesis and use of a second generation rationally designed Lewis-acid catalyst. Stereoselectivities of greater than 99.5% ee have been obtained for the Diels-Alder reaction of Subjects--Topical Terms:

516206
Chemistry, Organic.

The rational design of chiral alkyl dihaloboranes and their use as asymmetric Diels-Alder catalysts.
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008 130614s1994 eng d
035 $a (UnM)AAI9529506
035 $a AAI9529506
040 $a UnM $c UnM
100 1 $a Solow, Michael Alan. $3 1928500
245 1 4 $a The rational design of chiral alkyl dihaloboranes and their use as asymmetric Diels-Alder catalysts.
300 $a 194 p.
500 $a Source: Dissertation Abstracts International, Volume: 56-05, Section: B, page: 2638.
500 $a Chair: Joel M. Hawkins.
502 $a Thesis (Ph.D.)--University of California, Berkeley, 1994.
520 $a The Diels-Alder reaction, because of its highly ordered transition state and its ability to generate four stereocenters simultaneously, has become a testing ground for modern enantioselective catalysis. The rational design of a catalyst system can allow for variation and manipulation of attractive forces between catalyst and substrate which allow one to fine tune a catalyst system to be both active and stereoselective. This dissertation describes the synthesis and use of a second generation rationally designed Lewis-acid catalyst. Stereoselectivities of greater than 99.5% ee have been obtained for the Diels-Alder reaction of $\ alpha,\beta $- unsaturated esters and various dienes. Both $\ alpha $ and $\ beta $- substituted $\ alpha,\beta $- unsaturated esters have been explored. The enantioselectivity and endo/exo ratios of the reactions of cyclopentadiene with an assortment of crotonic esters have been compared. Other classes of dienophiles have also been investigated, including $\ alpha,\beta $- unsaturated ketones, aldehydes, acid chlorides, lactones, and anhydrides. Reactive conformations of the dienophile $\ cdot $c atalyst complexes have been proposed. A variety of cyclic and acyclic dienes have been used effectively.
590 $a School code: 0028.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Pharmaceutical. $3 550957
650 4 $a Chemistry, Inorganic. $3 517253
690 $a 0490
690 $a 0491
690 $a 0488
710 2 0 $a University of California, Berkeley. $3 687832
773 0 $t Dissertation Abstracts International $g 56-05B.
790 1 0 $a Hawkins, Joel M., $e advisor
790 $a 0028
791 $a Ph.D.
792 $a 1994
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9529506