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Enantioselective catalytic alkynylat...

Lu, Gui.

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Enantioselective catalytic alkynylation of carbonyl compounds.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Enantioselective catalytic alkynylation of carbonyl compounds./
Author:	Lu, Gui.
Description:	185 p.
Notes:	Source: Dissertation Abstracts International, Volume: 64-10, Section: B, page: 4945.
Contained By:	Dissertation Abstracts International64-10B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3107447
ISBN:	9780496549962

Enantioselective catalytic alkynylation of carbonyl compounds.
Lu, Gui.

Enantioselective catalytic alkynylation of carbonyl compounds. - 185 p.

Source: Dissertation Abstracts International, Volume: 64-10, Section: B, page: 4945.

Thesis (Ph.D.)--Hong Kong Polytechnic University (Hong Kong), 2003.

Chiral propargylic alcohols are useful building blocks for the enantioselective synthesis of high-valued pharmaceuticals intermediates. The preparation of propargylic alcohols via the addition of alkynes to aldehydes is of high interest because both the C-C bond and the chiral center can be formed in one step.

ISBN: 9780496549962Subjects--Topical Terms:

516206
Chemistry, Organic.

Enantioselective catalytic alkynylation of carbonyl compounds.
LDR:03383nam 2200337 a 45 001 948461
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020 $a 9780496549962
035 $a (UMI)AAI3107447
035 $a AAI3107447
040 $a UMI $c UMI
100 1 $a Lu, Gui. $3 1271921
245 1 0 $a Enantioselective catalytic alkynylation of carbonyl compounds.
300 $a 185 p.
500 $a Source: Dissertation Abstracts International, Volume: 64-10, Section: B, page: 4945.
500 $a Supervisors: Albert S. C. Chan; Wing Lai Chan.
502 $a Thesis (Ph.D.)--Hong Kong Polytechnic University (Hong Kong), 2003.
520 $a Chiral propargylic alcohols are useful building blocks for the enantioselective synthesis of high-valued pharmaceuticals intermediates. The preparation of propargylic alcohols via the addition of alkynes to aldehydes is of high interest because both the C-C bond and the chiral center can be formed in one step.
520 $a We have synthesized a series of amino alcohol ligands with binaphthyl backbones. One of these ligands was found to be highly effective in the asymmetric alkynylation of aldehydes. In the presence of dimethylzinc, a variety of aromatic aldehydes were converted to chiral propargylic alcohols in 61--93% e.e.
520 $a We have also developed a simple and practical method for the production of chiral propargylic alcohols from aldehydes and alkynes. In the presence of a titanium alkoxide catalyst prepared in situ from titanium tetraisopropoxide and (R)-H8-binaphthyl, a series of chiral propargylic alcohols were obtained with very good enantioselectivities (up to 96% e.e.) and yields. It was clear that the enantioselectivities of reactions catalyzed by (R)-H8-BINOL were higher than those obtained using (R)-BINOL. The new catalyst system is of particularly high scientific and practical interest owing to its simplicity, excellent enantioselectivity and high reactivity.
520 $a The self-assembly of several components into a highly enantioselective catalyst for asymmetric reaction is a new field in organic synthesis. We report here the first example of a chiral self-assembled titanium catalyst for asymmetric alkynylation, and the use of (S)-BINOL and chiral sulfonamide is proved to be the best combination in the reaction. Both the catalytic activity and enantioselectivity (99.7% e.e.) are substantially better than all previously reported catalysts.
520 $a In addition, the activation of chiral titanium (IV) complexes by achiral activators, e.g. phenol, was also found to provide higher levels of enantioselectivity than that attained by using enantiopure catalyst alone in the alkynylation of both aromatic and aliphatic aldehydes.
520 $a Asymmetric additions of alkynylzinc to aromatic ketones were carried out using a catalytic amount of chiral camphorsulfonamide and Cu(OTf) 2 to give tertiary propargylic alcohols in high yields and up to 97% e.e. To the best of our knowledge, this is the first report of the enantioselective addition of dialkynylzinc reagents to ketones.
590 $a School code: 1170.
650 4 $a Chemistry, Organic. $3 516206
690 $a 0490
710 2 $a Hong Kong Polytechnic University (Hong Kong). $3 1020200
773 0 $t Dissertation Abstracts International $g 64-10B.
790 $a 1170
790 1 0 $a Chan, Albert S. C., $e advisor
790 1 0 $a Chan, Wing Lai, $e advisor
791 $a Ph.D.
792 $a 2003
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3107447