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I. Asymmetric induction in heteroatom-substituted aldehydes. II. Total synthesis of (+)-casuarine.

Record Type:	Electronic resources : Monograph/item
Title/Author:	I. Asymmetric induction in heteroatom-substituted aldehydes. II. Total synthesis of (+)-casuarine.
Author:	Cee, Victor John.
Description:	459 p.
Notes:	Adviser: David A. Evans.
Notes:	Source: Dissertation Abstracts International, Volume: 64-05, Section: B, page: 2188.
Contained By:	Dissertation Abstracts International64-05B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3091526
ISBN:	0496392352

I. Asymmetric induction in heteroatom-substituted aldehydes. II. Total synthesis of (+)-casuarine.
Cee, Victor John.

I. Asymmetric induction in heteroatom-substituted aldehydes. II. Total synthesis of (+)-casuarine. [electronic resource] - 459 p.

Adviser: David A. Evans.

Thesis (Ph.D.)--Harvard University, 2003.

*Please refer to dissertation for diagrams.

ISBN: 0496392352Subjects--Topical Terms:

193634
Chemistry, Organic.

I. Asymmetric induction in heteroatom-substituted aldehydes. II. Total synthesis of (+)-casuarine.
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245 1 0 $a I. Asymmetric induction in heteroatom-substituted aldehydes. II. Total synthesis of (+)-casuarine. $h [electronic resource]
300 $a 459 p.
500 $a Adviser: David A. Evans.
500 $a Source: Dissertation Abstracts International, Volume: 64-05, Section: B, page: 2188.
502 $a Thesis (Ph.D.)--Harvard University, 2003.
520 # $a *Please refer to dissertation for diagrams.
520 # $a Aldol reactions of an oxygen-substituted enolate with oxygen-substituted aldehydes are described (eq 3). The two resulting vicinal oxygen stereocenters can be formed with a high degree of stereocontrol. Methods for the selective construction of several stereotetrads are identified.*
520 # $a An investigation of the impact of two oxygen stereocenters on aldehyde pi-facial selectivity in a systematic study of the aldol reaction between methyl ketone enolates and alpha,beta-alkoxy aldehydes is described (eq 2). The alpha,beta-anti-configured aldehyde exhibits consistently superior diastereoselectivity relative to the alpha,beta-syn-configured aldehyde. A model for this phenomenon is proposed. Methods for the selective construction of all possible stereotriads are identified.*
520 # $a I. Asymmetric Induction in Heteroatom-Substituted Aldehydes. A study of asymmetric induction in the aldol reaction between substituted enolate nucleophiles and chiral alpha-alkoxy aldehydes is described (eq 1). The results are inconsistent with a widely accepted model for asymmetric induction. A modified model is proposed. Theoretical support for this model at the ab initio level is presented.*
520 # $a II. Total Synthesis of (+)-Casuarine. The total synthesis of the polyhydroxylated pyrrolizidine alkaloid (+)-casuarine in nine steps and 28% overall yield is described (eq 4). The single alpha-amino stereocenter of a serine-derived aldehyde is used to control the configuration of five additional stereocenters in two aldol reactions of oxygen-substituted enolates.*
590 $a School code: 0084.
650 # 0 $a Chemistry, Organic. $3 193634
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773 0 # $g 64-05B. $t Dissertation Abstracts International
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791 $a Ph.D.
792 $a 2003
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