Synthesis of 1,3-dioxolanes by the addition of ketones to epoxides by using [Cp*Ir(NCMe)3]2+ as catalyst
Synthesis of 1,3-dioxolanes by the addition of ketones to epoxides by using [Cp*Ir(NCMe)3]2+ as catalyst
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DOI：
10.1016/s0022-328x(99)00039-x
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发表时间：
1999-06-20
影响因子：
2.3
通讯作者：
Brosius, K
中科院分区：
文献类型：
--
作者：
Adams, RD;Barnard, TS;Brosius, K
在[Cp*Ir（NCMe）（3）]（2+）（Cp*= C5 Me 5）催化下，酮与环氧化合物加成，合成了一系列1，3-二氧戊环。反应在22 ℃下容易进行，产率良好。以下1，3-二氧戊环：2，2，4-三甲基-1，3-二氧戊环，1; 2，2-二甲基-4-乙烯基-1，3-二氧戊环，2; 2，2-二甲基-4-苯基-1，3-二氧戊环，3; 2，2-二乙基-4-甲基-1，3-二氧戊环，4; 2，2-二乙基-4-乙烯基-1，3-二氧戊环，5; 2，2-二乙基-4-苯基-1，3-二氧戊环。6是由适当的环氧化物和羰基化合物制备的。在形成二氧戊环时，观察到在环氧化物的C-O键裂解位点的碳原子处发生构型反转：（R，S）-2，2，4，5-四甲基-1，3-二氧戊环，7和（R，R）-和（S，S）-2，2，4，5-四甲基-1，3-二氧戊环，8的混合物，其由丙酮与（R，R）-/（S，S）-丁烯-2-氧化物和R，S，-丁烯-2-氧化物。(C)1999年Elsevier Science S.A. All rights reserved.
A series of 1,3-dioxolanes have been prepared by the addition of ketones to epoxides in the presence of the catalyst [Cp*Ir(NCMe)(3)](2+), Cp*=C5Me5. The reactions proceed readily at 22 degrees C and the yields are good. The following 1,3-dioxolanes: 2,2,4-trimethyl-1,3-dioxolane, 1; 2,2-dimethyl-4-vinyl-1,3-dioxolane, 2; 2,2-dimethyl-4-phenyl-1,3-dioxolane, 3; 2,2-diethyl-4-methyl-1,3-dioxolane, 4; 2,2-diethyl-4-vinyl-1,3-dioxolane, 5; 2,2-diethyl-4-phenyl-1,3-dioxolane. 6 were prepared from the appropriate epoxide and carbonyl compounds. An inversion of configuration at the carbon atom at the C-O bond cleavage site of the epoxide was observed to occur in the formation of the dioxolanes: (R,S)- 2,2,4,5-tetramethyl-1,3-dioxolane, 7 and a mixture of (R,R)- and (S,S)-2,2,4,5-tetramethyl-1,3-dioxolane, 8 obtained from the reactions of acetone with (R,R)-/(S,S)-buten-2-oxide and R, S,-buten-2-oxide, respectively. (C) 1999 Elsevier Science S.A. All rights reserved.