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Enantioselective lanthanide-catalyze...

Wu, Jimmy.

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Enantioselective lanthanide-catalyzed Mukaiyama aldol, carbonyl-ene, Sakurai-Hosomi, and quinone Diels-Alder reactions.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Enantioselective lanthanide-catalyzed Mukaiyama aldol, carbonyl-ene, Sakurai-Hosomi, and quinone Diels-Alder reactions./
Author:	Wu, Jimmy.
Description:	303 p.
Notes:	Adviser: David A. Evans.
Contained By:	Dissertation Abstracts International66-11B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3194481
ISBN:	9780542392825

Enantioselective lanthanide-catalyzed Mukaiyama aldol, carbonyl-ene, Sakurai-Hosomi, and quinone Diels-Alder reactions.
Wu, Jimmy.

Enantioselective lanthanide-catalyzed Mukaiyama aldol, carbonyl-ene, Sakurai-Hosomi, and quinone Diels-Alder reactions. - 303 p.

Adviser: David A. Evans.

Thesis (Ph.D.)--Harvard University, 2005.

*Please refer to dissertation for diagrams.

ISBN: 9780542392825Subjects--Topical Terms:

516206
Chemistry, Organic.

Enantioselective lanthanide-catalyzed Mukaiyama aldol, carbonyl-ene, Sakurai-Hosomi, and quinone Diels-Alder reactions.
LDR:03622nam 2200325 a 45 001 948469
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020 $a 9780542392825
035 $a (UMI)AAI3194481
035 $a AAI3194481
040 $a UMI $c UMI
100 1 $a Wu, Jimmy. $3 1271929
245 1 0 $a Enantioselective lanthanide-catalyzed Mukaiyama aldol, carbonyl-ene, Sakurai-Hosomi, and quinone Diels-Alder reactions.
300 $a 303 p.
500 $a Adviser: David A. Evans.
500 $a Source: Dissertation Abstracts International, Volume: 66-11, Section: B, page: 5991.
502 $a Thesis (Ph.D.)--Harvard University, 2005.
520 $a *Please refer to dissertation for diagrams.
520 $a I. Asymmetric catalysis with chiral Sc complexes. Asymmetric transformations catalyzed by chiral scandium complexes have gained significant prominence in the last decade. This review encompasses enantioselective Sc(III)-catalyzed processes of general synthetic utility.
520 $a II. Sc-catalyzed Mukaiyama aldol reactions. Cationic scandium-based Lewis acid complexes have been found to catalyze the Mukaiyama aldol reaction between aryl enolsilanes and ethyl glyoxylate with high enantiomeric excesses (eq 1). The aldol adducts were converted to cis and trans beta,beta-dialkyl-gamma-substituted pantolactone derivatives using either a hydroxyl-directed syn or anti reduction, followed by acid-catalyzed lactonization (eq 2). Unsubstituted pantolactone derivatives were prepared by the hydrogenation of the corresponding thioester aldol adducts followed by cyclization. The required aldol products were also prepared using cationic scandium-based Lewis acid complexes.*
520 $a III. Sc-catalyzed carbonyl-ene reactions. An enantio- and diastereoselective carbonyl-ene reaction catalyzed by chiral scandium pyridyl-bis(oxazolinyl) (pybox) complexes has been developed (eq 3). 1,1-Disubstituted and trisubstituted olefins were efficient coupling partners with N-phenyl glyoxamide. The use of trisubstituted olefins generated the syn product while maintaining high levels of enantio- and diastereoselectivity. The scope of the copper bis(oxazolinyl) (box) mediated carbonyl-ene reaction has also been extended to include trisubstituted olefins. All products were highly crystalline solids.*
520 $a IV. Sc-catalyzed Sakurai-Hosomi reactions. An enantio- and diastereoselective Sakurai-Hosomi reaction catalyzed by chiral scandium pyridyl-bis(oxazoline) (pybox) complexes has been developed (eq 4). Both alkyl- and aryl-substituted allylic silanes were effective coupling partners with N-phenyl glyoxamide. Products were highly crystalline solids. In addition, an efficient one-step route for the preparation of (E)-cinnamyltrimethylsilane derivatives via an olefin-cross metathesis reaction is described.*
520 $a V. Sm- and Gd-catalyzed quinone Diels-Alder reactions. An enantioselective quinone Diels-Alder reaction catalyzed by chiral samarium and gadolinium pyridyl-bis(oxazolinyl) (pybox) complexes has been developed (eq 5). The permutations of reactions involving three quinones and five dienes were carried out with excellent enantio- and regioselectivities. These catalyst systems are able to distinguish very small steric differences between substituents found on the diene. In all cases, only the endo product is observed.*
590 $a School code: 0084.
650 4 $a Chemistry, Organic. $3 516206
690 $a 0490
710 2 $a Harvard University. $3 528741
773 0 $t Dissertation Abstracts International $g 66-11B.
790 $a 0084
790 1 0 $a Evans, David A., $e advisor
791 $a Ph.D.
792 $a 2005
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3194481