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Enantioselective alkylation of alpha...

Young, Brandon Michael.

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Enantioselective alkylation of alpha-imino esters catalyzed by chiral late transition metal phosphine complexes.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Enantioselective alkylation of alpha-imino esters catalyzed by chiral late transition metal phosphine complexes./
Author:	Young, Brandon Michael.
Description:	85 p.
Notes:	Source: Dissertation Abstracts International, Volume: 62-02, Section: B, page: 0869.
Subject:	Chemistry, Organic -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3006383
ISBN:	0493157271

Enantioselective alkylation of alpha-imino esters catalyzed by chiral late transition metal phosphine complexes.
Young, Brandon Michael.

Enantioselective alkylation of alpha-imino esters catalyzed by chiral late transition metal phosphine complexes. - 85 p.

Source: Dissertation Abstracts International, Volume: 62-02, Section: B, page: 0869.

Thesis (Ph.D.)--The Johns Hopkins University, 2001.

Catalytic, asymmetric transformations of imines are a timely challenge in organic synthesis. This thesis details methodology for the enantioselective transformations of N-tosyl α-imino esters using catalytic amounts of chiral Lewis acids. Our approach focuses on the use of chiral late transition metal phosphine complexes to control the alkylation of imino esters with a variety of nucleophiles including enol silanes, ketene acetals, allyl silanes, and alkenes. Using very low catalyst loads (1–5 mol%), nonnatural amino acid derivatives are produced in high yield with high enantioselectivity (up to 99% ee) and diastereoselectivity (up to 25:1 <italic>anti:syn</italic>). These amino acid derivatives are important precursors in the synthesis of complex natural products as well as pharmaceutically active compounds. Transition state models are proposed to account for the diastereoselectivity seen using substituted enol silanes. In addition, mechanistic studies perform that the reaction proceeds through classic Lewis acid activation rather than by means of catalytic, chiral metal-based enolates. Other mechanistic studies reveal the role of the catalyst in increasing the reaction rate as well as inhibition of the catalyst by the reaction products.

ISBN: 0493157271Subjects--Topical Terms:

1941635
Chemistry, Organic

Enantioselective alkylation of alpha-imino esters catalyzed by chiral late transition metal phosphine complexes.
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020 $a 0493157271
035 $a (UnM)AAI3006383
035 $a AAI3006383
040 $a UnM $c UnM
100 1 $a Young, Brandon Michael. $3 1941634
245 1 0 $a Enantioselective alkylation of alpha-imino esters catalyzed by chiral late transition metal phosphine complexes.
300 $a 85 p.
500 $a Source: Dissertation Abstracts International, Volume: 62-02, Section: B, page: 0869.
500 $a Adviser: Thomas Lectka.
502 $a Thesis (Ph.D.)--The Johns Hopkins University, 2001.
520 $a Catalytic, asymmetric transformations of imines are a timely challenge in organic synthesis. This thesis details methodology for the enantioselective transformations of N-tosyl α-imino esters using catalytic amounts of chiral Lewis acids. Our approach focuses on the use of chiral late transition metal phosphine complexes to control the alkylation of imino esters with a variety of nucleophiles including enol silanes, ketene acetals, allyl silanes, and alkenes. Using very low catalyst loads (1–5 mol%), nonnatural amino acid derivatives are produced in high yield with high enantioselectivity (up to 99% ee) and diastereoselectivity (up to 25:1 <italic>anti:syn</italic>). These amino acid derivatives are important precursors in the synthesis of complex natural products as well as pharmaceutically active compounds. Transition state models are proposed to account for the diastereoselectivity seen using substituted enol silanes. In addition, mechanistic studies perform that the reaction proceeds through classic Lewis acid activation rather than by means of catalytic, chiral metal-based enolates. Other mechanistic studies reveal the role of the catalyst in increasing the reaction rate as well as inhibition of the catalyst by the reaction products.
590 $a School code: 0098.
650 4 $a Chemistry, Organic $3 1941635
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3006383