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Molybdenum-catalyzed asymmetric alke...

Cefalo, Dustin Robert.

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Molybdenum-catalyzed asymmetric alkene metathesis and applications to organic synthesis.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Molybdenum-catalyzed asymmetric alkene metathesis and applications to organic synthesis./
Author:	Cefalo, Dustin Robert.
Description:	252 p.
Notes:	Source: Dissertation Abstracts International, Volume: 64-08, Section: B, page: 3824.
Contained By:	Dissertation Abstracts International64-08B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3103260
ISBN:	0496508281

Molybdenum-catalyzed asymmetric alkene metathesis and applications to organic synthesis.
Cefalo, Dustin Robert.

Molybdenum-catalyzed asymmetric alkene metathesis and applications to organic synthesis. - 252 p.

Source: Dissertation Abstracts International, Volume: 64-08, Section: B, page: 3824.

Thesis (Ph.D.)--Boston College, 2003.

Catalytic kinetic resolution. Mo-complex 3 is first example of a chiral metathesis that was able to efficiently resolve racemic 1,5-dienes through asymmetric ring-closing metathesis (ARCM). These reactions provide non-racemic dienes as well as optically enriched carbo- and heterocyclic products. Either the diene substrate or the ring-closed product can be obtained in high yields and optical purities (k rel up to 58). Interestingly, when 1,6-dienes are subjected to either catalyst 3 or 4 the product formed is obtained with <5% ee.*

ISBN: 0496508281Subjects--Topical Terms:

516206
Chemistry, Organic.

Molybdenum-catalyzed asymmetric alkene metathesis and applications to organic synthesis.
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100 1 $a Cefalo, Dustin Robert. $3 1928576
245 1 0 $a Molybdenum-catalyzed asymmetric alkene metathesis and applications to organic synthesis.
300 $a 252 p.
500 $a Source: Dissertation Abstracts International, Volume: 64-08, Section: B, page: 3824.
500 $a Adviser: Amir H. Hoveyda.
502 $a Thesis (Ph.D.)--Boston College, 2003.
520 $a Catalytic kinetic resolution. Mo-complex 3 is first example of a chiral metathesis that was able to efficiently resolve racemic 1,5-dienes through asymmetric ring-closing metathesis (ARCM). These reactions provide non-racemic dienes as well as optically enriched carbo- and heterocyclic products. Either the diene substrate or the ring-closed product can be obtained in high yields and optical purities (k rel up to 58). Interestingly, when 1,6-dienes are subjected to either catalyst 3 or 4 the product formed is obtained with <5% ee.*
520 $a Catalytic enantioselective desymmetrization. In another approach, it was found that achiral trienes could be subjected to complex 3 or 4 to afford optically pure products in high yields. These catalytic reactions can be run with very low catalyst loading (1--2 mol%) and in the absence of solvent to provide the desired product in optical purity and with high yields.
520 $a Catalytic enantioselective six membered ring synthesis. The modularity of the Mo-based catalysts allows for the synthesis of a large variety of products. When catalyst 3 is used to synthesize six membered rings, inferior asymmetric induction is observed. In contrast, when the biphenol ligand was changed to the triisopropylphenyl substituted binaphol moiety (complex 5), catalytic ring-closing metatheses proceed with outstanding enantioselectivity. Once again, these efficient asymmetric processes can be run in the absence of solvent to yield products in 98% isolated yield and >99 %ee.*
520 $a Catalytic enantioselective asymmetric ring-opening metathesis. The desire to apply the asymmetric metathesis methodology to the synthesis of medicinally important molecules led us to explore the development of asymmetric ring-opening metathesis towards forming optically pure tertiary ethers. It was found that catalyst 5 was effective in providing dihydropyrans in high yield and with high ee. The formation of optically enriched spirocycles is effectively catalyzed by complex 6 bearing a 2,6-dichloroimido ligand. This new catalytic enantioselective protocol is being applied to the asymmetric total synthesis of the HIV protease inhibitor tipranavir.*
520 $a *Please refer to dissertation for diagrams.
590 $a School code: 0016.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Inorganic. $3 517253
690 $a 0490
690 $a 0488
710 2 0 $a Boston College. $3 1017525
773 0 $t Dissertation Abstracts International $g 64-08B.
790 1 0 $a Hoveyda, Amir H., $e advisor
790 $a 0016
791 $a Ph.D.
792 $a 2003
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3103260