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Catalytic, enantioselective alkylati...

Ferraris, Dana.

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Catalytic, enantioselective alkylation of alpha-imino esters: The synthesis of nonnatural alpha-amino acid derivatives.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Catalytic, enantioselective alkylation of alpha-imino esters: The synthesis of nonnatural alpha-amino acid derivatives./
Author:	Ferraris, Dana.
Description:	88 p.
Notes:	Adviser: Thomas Lectka.
Contained By:	Dissertation Abstracts International60-11B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9950519
ISBN:	9780599528215

Catalytic, enantioselective alkylation of alpha-imino esters: The synthesis of nonnatural alpha-amino acid derivatives.
Ferraris, Dana.

Catalytic, enantioselective alkylation of alpha-imino esters: The synthesis of nonnatural alpha-amino acid derivatives. - 88 p.

Adviser: Thomas Lectka.

Thesis (Ph.D.)--The Johns Hopkins University, 2000.

Methodology for the practical synthesis of nonnatural amino acids has been developed via the alkylation of imino esters and N, O-acetals with enol silanes, ketene acetals, allyl silanes and olefins using transition metalphosphine complexes as catalysts (1--5 mol %). The alkylation products are prepared with high enantioselectivities (up to 99% ee) and anti diastereoselectivities (up to 25:1/anti:syn). These protected nonnatural amino acids are precursors to important natural products and pharmaceuticals. We provide mechanistic data and stereochemical models to account for the enantio- and diastereoselectivity of these alkylations. In addition, transition states are proposed for the asymmetric alkylation with enol silanes, allyl silanes and the imino ene reaction. Kinetic data and isotope effects from the imino ene reaction are used to determine the reaction mechanism and the effect of catalyst loadings and product inhibition on the rate of reaction.

ISBN: 9780599528215Subjects--Topical Terms:

516206
Chemistry, Organic.

Catalytic, enantioselective alkylation of alpha-imino esters: The synthesis of nonnatural alpha-amino acid derivatives.
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100 1 $a Ferraris, Dana. $3 1297803
245 1 0 $a Catalytic, enantioselective alkylation of alpha-imino esters: The synthesis of nonnatural alpha-amino acid derivatives.
300 $a 88 p.
500 $a Adviser: Thomas Lectka.
500 $a Source: Dissertation Abstracts International, Volume: 60-11, Section: B, page: 5520.
502 $a Thesis (Ph.D.)--The Johns Hopkins University, 2000.
520 $a Methodology for the practical synthesis of nonnatural amino acids has been developed via the alkylation of imino esters and N, O-acetals with enol silanes, ketene acetals, allyl silanes and olefins using transition metalphosphine complexes as catalysts (1--5 mol %). The alkylation products are prepared with high enantioselectivities (up to 99% ee) and anti diastereoselectivities (up to 25:1/anti:syn). These protected nonnatural amino acids are precursors to important natural products and pharmaceuticals. We provide mechanistic data and stereochemical models to account for the enantio- and diastereoselectivity of these alkylations. In addition, transition states are proposed for the asymmetric alkylation with enol silanes, allyl silanes and the imino ene reaction. Kinetic data and isotope effects from the imino ene reaction are used to determine the reaction mechanism and the effect of catalyst loadings and product inhibition on the rate of reaction.
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650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Pharmaceutical. $3 550957
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710 2 0 $a The Johns Hopkins University. $3 1017431
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856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9950519