Lanthanum tricyanide-catalyzed acyl silane-ketone benzoin additions and kinetic resolution of resultant alpha-silyloxyketones.
Lanthanum tricyanide-catalyzed acyl silane-ketone benzoin additions and kinetic resolution of resultant alpha-silyloxyketones.
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DOI：
10.1021/jo100312w
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发表时间：
2010-05-21
影响因子：
3.6
通讯作者：
Johnson, Jeffrey S.
中科院分区：
文献类型：
--
作者：
Tarr, James C.;Johnson, Jeffrey S.
We report the full account of our efforts on the lanthanum tricyanide-catalyzed acyl silane-ketone benzoin reaction. The reaction exhibits a wide scope in both acyl silane (aryl, alkyl) and ketone (aryl-alkyl, alkyl-alkyl, aryl-aryl, alkenyl-alkyl, alkynyl-alkyl) coupling partners. The diastereoselectivity of the reaction has been examined in both cyclic and acyclic systems. Cyclohexanones give products arising from equatorial attack by the acyl silane. The diastereoselectivity of acyl silane addition to acyclic α-hydroxy ketones can be controlled by varying the protecting group to obtain either Felkin-Ahn or chelation control. The resultant α-silyloxyketone products can be resolved with selectivity factors from 10 to 15 by subjecting racemic ketone benzoin products to CBS reduction.
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影响因子：
3.6
作者：
Demir, Ayhan S.;Reis, Barbaros;Saglam, Gueluezar
通讯作者：
Saglam, Gueluezar
DOI：
10.1139/v90-266
发表时间：
1990-10-01
期刊：
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE
影响因子：
--
作者：
BORDWELL, FG;HARRELSON, JA
通讯作者：
HARRELSON, JA
影响因子：
16.6
作者：
Enders, D;Niemeier, O;Balensiefer, T
通讯作者：
Balensiefer, T
影响因子：
15
作者：
Chiang, Pei-Chen;Kaeobamrung, Juthanat;Bode, Jeffrey W.
通讯作者：
Bode, Jeffrey W.
影响因子：
--
作者：
Dorizon, P;Martin, C;Kagan, HB
通讯作者：
Kagan, HB