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Studies toward asymmetric ketone hyd...

Kalberg, Christopher Scott.

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Studies toward asymmetric ketone hydrogenation.

紀錄類型:	書目-語言資料,印刷品 : Monograph/item
正題名/作者:	Studies toward asymmetric ketone hydrogenation./
作者:	Kalberg, Christopher Scott.
面頁冊數:	135 p.
附註:	Source: Dissertation Abstracts International, Volume: 59-08, Section: B, page: 4103.
Contained By:	Dissertation Abstracts International59-08B.
標題:	Chemistry, Inorganic. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9903813
ISBN:	9780599010833

Studies toward asymmetric ketone hydrogenation.
Kalberg, Christopher Scott.

Studies toward asymmetric ketone hydrogenation. - 135 p.

Source: Dissertation Abstracts International, Volume: 59-08, Section: B, page: 4103.

Thesis (Ph.D.)--Duke University, 1998.

Catalytic asymmetric hydrogenation methodology has proven to be a powerful tool in the synthesis of small chiral building blocks, particularly, amino acids and amino acid derivatives. Extension of this method to the synthesis of other classes of useful chiral small molecules such as the $\beta$-hydroxy esters and the $\alpha$-hydroxy esters is demonstrated.

ISBN: 9780599010833Subjects--Topical Terms:

517253
Chemistry, Inorganic.

Studies toward asymmetric ketone hydrogenation.
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100 1 $a Kalberg, Christopher Scott. $3 1297796
245 1 0 $a Studies toward asymmetric ketone hydrogenation.
300 $a 135 p.
500 $a Source: Dissertation Abstracts International, Volume: 59-08, Section: B, page: 4103.
500 $a Supervisor: Steven W. Baldwin.
502 $a Thesis (Ph.D.)--Duke University, 1998.
520 $a Catalytic asymmetric hydrogenation methodology has proven to be a powerful tool in the synthesis of small chiral building blocks, particularly, amino acids and amino acid derivatives. Extension of this method to the synthesis of other classes of useful chiral small molecules such as the $\beta$-hydroxy esters and the $\alpha$-hydroxy esters is demonstrated.
520 $a The i-Pr-BPE-Ru catalyst system was shown to be effective for the hydrogenation of a wide range $\beta$-keto esters under mild conditions. The corresponding $\beta$-hydroxy esters were thus obtained in quantitative yield with enantioselectivities generally $> $9 8% e.e. Among other uses, the chiral $\beta$-hydroxy esters are utilized in the synthesis of the chiral BPE ligands employed for the hydrogenation. To this end, (R) methyl 3-cyclohexyl-3-hydroxy propanoate was used in the synthesis of the new (S,S)-CyBPE ligand which was also shown to be effective for hydrogenation of $\beta$-keto esters.
520 $a Our focus was then turned to the synthesis of the more desirable, if not more difficult, $\alpha$-hydroxy esters. Direct hydrogenation of the corresponding $\alpha$-keto esters proved fruitless, with both yield and enantioselectivity being less than desirable. The use of enol esters as hydrogenation substrates was shown to circumvent this problem and a wide range of protected $\alpha$-hydroxy esters were obtained in excellent yield with enantioselectivities of $> $9 5% e.e. Deprotection to yield the desired $\alpha$-hydroxy esters was shown to proceed without loss of stereochemical integrity. Reduction to the corresponding 1,2-diols with retention of stereochemistry was also demonstrated.
590 $a School code: 0066.
650 4 $a Chemistry, Inorganic. $3 517253
650 4 $a Chemistry, Organic. $3 516206
690 $a 0488
690 $a 0490
710 2 0 $a Duke University. $3 569686
773 0 $t Dissertation Abstracts International $g 59-08B.
790 $a 0066
790 1 0 $a Baldwin, Steven W., $e advisor
791 $a Ph.D.
792 $a 1998
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