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I. Asymmetric induction in heteroatom-substituted aldehydes. II. Total synthesis of (+)-casuarine.
紀錄類型:
書目-電子資源 : Monograph/item
正題名/作者:
I. Asymmetric induction in heteroatom-substituted aldehydes. II. Total synthesis of (+)-casuarine.
作者:
Cee, Victor John.
面頁冊數:
459 p.
附註:
Adviser: David A. Evans.
附註:
Source: Dissertation Abstracts International, Volume: 64-05, Section: B, page: 2188.
Contained By:
Dissertation Abstracts International64-05B.
標題:
Chemistry, Organic.
電子資源:
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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459 p.
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Source: Dissertation Abstracts International, Volume: 64-05, Section: B, page: 2188.
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Thesis (Ph.D.)--Harvard University, 2003.
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*Please refer to dissertation for diagrams.
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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.*
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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.*
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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.*
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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.*
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