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The Development of New Catalysts for...

Hu, Bin.

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The Development of New Catalysts for Asymmetric Umpolung Reactions Generating Chiral Amines.

Record Type:	Electronic resources : Monograph/item
Title/Author:	The Development of New Catalysts for Asymmetric Umpolung Reactions Generating Chiral Amines./
Author:	Hu, Bin.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2019,
Description:	398 p.
Notes:	Source: Dissertation Abstracts International, Volume: 80-08(E), Section: B.
Contained By:	Dissertation Abstracts International80-08B(E).
Subject:	Chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10977919
ISBN:	9781392020234

The Development of New Catalysts for Asymmetric Umpolung Reactions Generating Chiral Amines.
Hu, Bin.

The Development of New Catalysts for Asymmetric Umpolung Reactions Generating Chiral Amines. - Ann Arbor : ProQuest Dissertations & Theses, 2019 - 398 p.

Source: Dissertation Abstracts International, Volume: 80-08(E), Section: B.

Thesis (Ph.D.)--Brandeis University, 2019.

Chiral gamma-amino acids are present as a structural motif in a wide variety of biologically interesting natural products and synthetic compounds. We discovered that novel cinchona alkaloid-derived chiral phase transfer catalysts could enable the highly chemo-, regio-, diastereo-, and enantioselective umpolung addition of trifluoromethyl imines to alpha, beta-unsaturated N-acyl pyrroles. With a catalyst loading ranging from 0.2 to 5.0 mol%, this new catalytic asymmetric transformation provides facile and high-yielding access to highly enantiomerically enriched chiral trifluoromethyl gamma-amino acids and gamma-lactams.

ISBN: 9781392020234Subjects--Topical Terms:

516420
Chemistry.

The Development of New Catalysts for Asymmetric Umpolung Reactions Generating Chiral Amines.
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245 1 4 $a The Development of New Catalysts for Asymmetric Umpolung Reactions Generating Chiral Amines.
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300 $a 398 p.
500 $a Source: Dissertation Abstracts International, Volume: 80-08(E), Section: B.
500 $a Adviser: Li Deng.
502 $a Thesis (Ph.D.)--Brandeis University, 2019.
520 $a Chiral gamma-amino acids are present as a structural motif in a wide variety of biologically interesting natural products and synthetic compounds. We discovered that novel cinchona alkaloid-derived chiral phase transfer catalysts could enable the highly chemo-, regio-, diastereo-, and enantioselective umpolung addition of trifluoromethyl imines to alpha, beta-unsaturated N-acyl pyrroles. With a catalyst loading ranging from 0.2 to 5.0 mol%, this new catalytic asymmetric transformation provides facile and high-yielding access to highly enantiomerically enriched chiral trifluoromethyl gamma-amino acids and gamma-lactams.
520 $a Cinchona alkaloid-derived chiral catalysts represent one of the most widely applied class of organocatalysts in asymmetric synthesis which have been successfully utilized in the promotion of a wide variety of asymmetric reactions. Due to the structurally pseudoenantiomeric properties, these catalysts could also fail to mediate the formation of desired both enantiomers with similarly high enantioselectivities and yields. Based on several key insights gained from X-ray crystal structural studies, we described here an unprecedented general modification of these natural cinchona scaffold which enabled us to realize a series of highly efficient and enantioselective reactions for the direct generation of opposite enantiomers in high yields and enantioselectivities. More impressively, these newly developed catalysts demonstrated significantly improved catalytic capability compared with all the natural-originated cinchona catalysts.
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