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Catalytic Asymmetric Multi-Component...

Dai, Yijing.

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Catalytic Asymmetric Multi-Component Kabachnik-Fields Reaction by Vanol-Derived Zirconium Complex and Total Synthesis of Sphingoid Bases.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Catalytic Asymmetric Multi-Component Kabachnik-Fields Reaction by Vanol-Derived Zirconium Complex and Total Synthesis of Sphingoid Bases./
Author:	Dai, Yijing.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2018,
Description:	230 p.
Notes:	Source: Dissertations Abstracts International, Volume: 79-12, Section: B.
Contained By:	Dissertations Abstracts International79-12B.
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10817425
ISBN:	9780438009608

Catalytic Asymmetric Multi-Component Kabachnik-Fields Reaction by Vanol-Derived Zirconium Complex and Total Synthesis of Sphingoid Bases.
Dai, Yijing.

Catalytic Asymmetric Multi-Component Kabachnik-Fields Reaction by Vanol-Derived Zirconium Complex and Total Synthesis of Sphingoid Bases. - Ann Arbor : ProQuest Dissertations & Theses, 2018 - 230 p.

Source: Dissertations Abstracts International, Volume: 79-12, Section: B.

Thesis (Ph.D.)--Michigan State University, 2018.

This item must not be sold to any third party vendors.

A highly efficient asymmetric catalytic approach to synthesize -amino phosphonates by employing aldehydes, amines and diethyl phosphites under a chiral VANOL-derived zirconium complex was developed. The asymmetric induction of this direct three-component hydrophosphonylation reaction (Kabachnik-Fields reaction) of aliphatic aldehydes reaches over 90% ee for the first time. Broad scope of aromatic and aliphatic substrates bearing various functional groups including silyl ether, ester, amide, olefin, alkyne, azide etc. can be tolerated under the reaction conditions with good yield and ee. In the preliminary mechanism study, it was found that the 2-hydroxyl group on the aniline is crucial to the introduction of the enantioselectivity. Sphingoid bases are backbones of new class sphingolipids and they have four different members present in two-headed family with similar structure, but with different stereochemistry. The key step in the synthesis of sphingoid bases are nucleophilic addition between two heads and highly enantioselective trans- / cis-asymmetric aziridination, which is for setting four chiral centers in the structures.

ISBN: 9780438009608Subjects--Topical Terms:

523952
Organic chemistry.

Catalytic Asymmetric Multi-Component Kabachnik-Fields Reaction by Vanol-Derived Zirconium Complex and Total Synthesis of Sphingoid Bases.
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100 1 $a Dai, Yijing. $3 3434558
245 1 0 $a Catalytic Asymmetric Multi-Component Kabachnik-Fields Reaction by Vanol-Derived Zirconium Complex and Total Synthesis of Sphingoid Bases.
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300 $a 230 p.
500 $a Source: Dissertations Abstracts International, Volume: 79-12, Section: B.
500 $a Publisher info.: Dissertation/Thesis.
500 $a Advisor: Wulff, William D.
502 $a Thesis (Ph.D.)--Michigan State University, 2018.
506 $a This item must not be sold to any third party vendors.
520 $a A highly efficient asymmetric catalytic approach to synthesize -amino phosphonates by employing aldehydes, amines and diethyl phosphites under a chiral VANOL-derived zirconium complex was developed. The asymmetric induction of this direct three-component hydrophosphonylation reaction (Kabachnik-Fields reaction) of aliphatic aldehydes reaches over 90% ee for the first time. Broad scope of aromatic and aliphatic substrates bearing various functional groups including silyl ether, ester, amide, olefin, alkyne, azide etc. can be tolerated under the reaction conditions with good yield and ee. In the preliminary mechanism study, it was found that the 2-hydroxyl group on the aniline is crucial to the introduction of the enantioselectivity. Sphingoid bases are backbones of new class sphingolipids and they have four different members present in two-headed family with similar structure, but with different stereochemistry. The key step in the synthesis of sphingoid bases are nucleophilic addition between two heads and highly enantioselective trans- / cis-asymmetric aziridination, which is for setting four chiral centers in the structures.
590 $a School code: 0128.
650 4 $a Organic chemistry. $3 523952
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710 2 $a Michigan State University. $b Chemistry. $3 1682179
773 0 $t Dissertations Abstracts International $g 79-12B.
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