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Ruthenium and palladium catalyzed me...

Machacek, Michelle Rae.

Ruthenium and palladium catalyzed methods for complex tetrahydropyran synthesis.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Ruthenium and palladium catalyzed methods for complex tetrahydropyran synthesis.
Author:	Machacek, Michelle Rae.
Description:	503 p.
Notes:	Adviser: Barry M. Trost.
Notes:	Source: Dissertation Abstracts International, Volume: 66-01, Section: B, page: 0284.
Contained By:	Dissertation Abstracts International66-01B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3162399
ISBN:	0496964631

Ruthenium and palladium catalyzed methods for complex tetrahydropyran synthesis.
Machacek, Michelle Rae.

Ruthenium and palladium catalyzed methods for complex tetrahydropyran synthesis. - 503 p.

Adviser: Barry M. Trost.

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

Application of the ruthenium catalyzed ene-yne coupling reaction to a one-pot synthesis of both oxygen and nitrogen-containing heterocycles is described. Ene-yne coupling is followed by allylic substitution to yield cyclized products. The scope of the reaction is limited when ruthenium catalyzes both steps in tandem. However, the scope is greatly expanded when palladium catalysis is used for the allylic substitution step. A one-pot two-metal enantioselective process is developed where issues of compatibility of the two catalysts is addressed. The scope and high enantioselectivity of the cyclization is demonstrated. Furthermore, the ability to use simple alkyl alcohols as nucleophiles in palladium catalyzed asymmetric allylic alkylation reactions is demonstrated.

ISBN: 0496964631Subjects--Topical Terms:

193634
Chemistry, Organic.

Ruthenium and palladium catalyzed methods for complex tetrahydropyran synthesis.
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100 0 $a Machacek, Michelle Rae. $3 237463
245 1 0 $a Ruthenium and palladium catalyzed methods for complex tetrahydropyran synthesis.
300 $a 503 p.
500 $a Adviser: Barry M. Trost.
500 $a Source: Dissertation Abstracts International, Volume: 66-01, Section: B, page: 0284.
502 $a Thesis (Ph.D.)--Stanford University, 2005.
520 # $a Application of the ruthenium catalyzed ene-yne coupling reaction to a one-pot synthesis of both oxygen and nitrogen-containing heterocycles is described. Ene-yne coupling is followed by allylic substitution to yield cyclized products. The scope of the reaction is limited when ruthenium catalyzes both steps in tandem. However, the scope is greatly expanded when palladium catalysis is used for the allylic substitution step. A one-pot two-metal enantioselective process is developed where issues of compatibility of the two catalysts is addressed. The scope and high enantioselectivity of the cyclization is demonstrated. Furthermore, the ability to use simple alkyl alcohols as nucleophiles in palladium catalyzed asymmetric allylic alkylation reactions is demonstrated.
520 # $a The ability to use simple alkyl alcohols as nucleophiles in palladium catalyzed dynamic kinetic asymmetric transformations is described. Further development of simple alkyl alcohol nucleophiles in the context of a deracemization of Baylis-Hillman adducts is investigated. Both kinetic resolution and dynamic kinetic resolution processes are obtained depending on reaction conditions. The utility of this method is demonstrated in a total synthesis of (+)-hippospongic acid A. The synthesis is completed in 15 linear steps featuring three palladium catalyzed allylic substitution reactions.
520 # $a The utility of this one-pot two-metal process is demonstrated in the context of total synthesis. A concise synthesis of ring B of the bryostatin family is described. The approach efficiently sets the stereochemistry of the trisubstituted enone of ring B. Progress towards the synthesis of (-)-dactylolide is also described. The southern portion of the molecule is expediently synthesized using the one-pot two-metal synthesis of heterocycles to afford the pyran moiety, followed by a ruthenium catalyzed ene-yne coupling reaction to form the trisubstituted olefin in the macrocyclic ring.
520 # $a Trimethylsilylalkynes undergo highly chemo- and regioselective coupling with terminal alkenes in the presence of [CpRu(CH3CN)3]PF 6 to form stereodefined 1,4-diene products in good yield. The scope and functional group tolerance of this reaction is described. Combining the ruthenium catalyzed ene-yne coupling reaction with palladium catalyzed silicon cross-coupling allows access to a variety of trisubstituted alkenes with defined geometry. The development of benzyldimethylsilane as a robust, yet activated silane for cross-coupling is illustrated.
590 $a School code: 0212.
650 # 0 $a Chemistry, Organic. $3 193634
690 $a 0490
710 0 # $a Stanford University. $3 212607
773 0 # $g 66-01B. $t Dissertation Abstracts International
790 $a 0212
790 1 0 $a Trost, Barry M., $e advisor
791 $a Ph.D.
792 $a 2005
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