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Asymmetric catalytic epoxide ring-op...

Kim, Sang Kyun.

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Asymmetric catalytic epoxide ring-opening reactions: Synthesis of highly enantiomerically enriched terminal aziridines, O-(2-hydroxyalkyl)oxime ethers, 1,2-aminooxy alcohols.

紀錄類型:	書目-語言資料,印刷品 : Monograph/item
正題名/作者:	Asymmetric catalytic epoxide ring-opening reactions: Synthesis of highly enantiomerically enriched terminal aziridines, O-(2-hydroxyalkyl)oxime ethers, 1,2-aminooxy alcohols./
作者:	Kim, Sang Kyun.
面頁冊數:	102 p.
附註:	Adviser: Eric N. Jacobsen.
Contained By:	Dissertation Abstracts International67-02B.
標題:	Chemistry, Organic. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3205916
ISBN:	9780542547058

Asymmetric catalytic epoxide ring-opening reactions: Synthesis of highly enantiomerically enriched terminal aziridines, O-(2-hydroxyalkyl)oxime ethers, 1,2-aminooxy alcohols.
Kim, Sang Kyun.

Asymmetric catalytic epoxide ring-opening reactions: Synthesis of highly enantiomerically enriched terminal aziridines, O-(2-hydroxyalkyl)oxime ethers, 1,2-aminooxy alcohols. - 102 p.

Adviser: Eric N. Jacobsen.

Thesis (Ph.D.)--Harvard University, 2006.

I. General catalytic synthesis of highly enantiomerically enriched terminal aziridines. Asymmetric synthesis of N-Ns- and N-SES-protected terminal aziridines was achieved by an indirect kinetic resolution process. Low selectivity in the [(salen)Co]-catalyzed kinetic resolution of terminal epoxides with N-Boc sulfonamides was parlayed into an efficient one-pot synthesis of enantiopure amino alcohol derivatives by hydrolytic kinetic resolution (HKR) followed by ring-opening of the "mismatched", unreacted enantiomer of the epoxide by a sulfonamide derivative promoted by the same catalyst. The resulting amino alcohols were converted to terminal aziridines by Boc-deprotection/mesylation/cyclization. A variety of terminal aziridines were thus synthesized in 58--86% overall yield and 98.8->99% ee (13 examples). Enantiopure N-Ns- and N-SES-chloromethylaziridine were synthesized for the first time and were used in the synthesis of other enantiopure terminal aziridines and in a three step route to 3-aminotetrahydroquinoline. The mechanism of the reaction between terminal epoxides and N-Boc sulfonamide catalyzed by [(salen)Co] was investigated using a range of kinetic techniques. A distinctive mechanism involving nucleophile activation by catalyst and epoxide activation by the nucleophile is proposed.

ISBN: 9780542547058Subjects--Topical Terms:

516206
Chemistry, Organic.

Asymmetric catalytic epoxide ring-opening reactions: Synthesis of highly enantiomerically enriched terminal aziridines, O-(2-hydroxyalkyl)oxime ethers, 1,2-aminooxy alcohols.
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100 1 $a Kim, Sang Kyun. $3 1271935
245 1 0 $a Asymmetric catalytic epoxide ring-opening reactions: Synthesis of highly enantiomerically enriched terminal aziridines, O-(2-hydroxyalkyl)oxime ethers, 1,2-aminooxy alcohols.
300 $a 102 p.
500 $a Adviser: Eric N. Jacobsen.
500 $a Source: Dissertation Abstracts International, Volume: 67-02, Section: B, page: 0892.
502 $a Thesis (Ph.D.)--Harvard University, 2006.
520 $a I. General catalytic synthesis of highly enantiomerically enriched terminal aziridines. Asymmetric synthesis of N-Ns- and N-SES-protected terminal aziridines was achieved by an indirect kinetic resolution process. Low selectivity in the [(salen)Co]-catalyzed kinetic resolution of terminal epoxides with N-Boc sulfonamides was parlayed into an efficient one-pot synthesis of enantiopure amino alcohol derivatives by hydrolytic kinetic resolution (HKR) followed by ring-opening of the "mismatched", unreacted enantiomer of the epoxide by a sulfonamide derivative promoted by the same catalyst. The resulting amino alcohols were converted to terminal aziridines by Boc-deprotection/mesylation/cyclization. A variety of terminal aziridines were thus synthesized in 58--86% overall yield and 98.8->99% ee (13 examples). Enantiopure N-Ns- and N-SES-chloromethylaziridine were synthesized for the first time and were used in the synthesis of other enantiopure terminal aziridines and in a three step route to 3-aminotetrahydroquinoline. The mechanism of the reaction between terminal epoxides and N-Boc sulfonamide catalyzed by [(salen)Co] was investigated using a range of kinetic techniques. A distinctive mechanism involving nucleophile activation by catalyst and epoxide activation by the nucleophile is proposed.
520 $a II. Asymmetric catalytic synthesis of O-(2-Hydroxyalkyl)oxime ethers and 1,2-aminooxy alcohols. A highly enantioselective route to O-(2-hydroxyalkyl)oxime ethers and 1,2-aminooxy alcohols was developed using an oligomeric [(salen)Co] catalyst. Kinetic resolution of terminal racemic epoxides was achieved with arylaldoximes, ketoximes, and hydroxylamine derivatives as nucleophilic partners. The desired oxime ethers and 1,2-aminooxy alcohols were synthesized in 90--100% yield and 98--99.8% ee (12 examples). Alkylaldoxime ether derivatives were not accessible by this route, but they could be prepared efficiently from the corresponding N-Boc-protected aminooxy alcohols.
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650 4 $a Chemistry, Organic. $3 516206
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773 0 $t Dissertation Abstracts International $g 67-02B.
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791 $a Ph.D.
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