Synthesis and catalytic properties of 4-aryl-2,3-dihydro-4H-pyrimido[2,3-b]benzothiazoles for asymmetric acyl or carboxyl group transfer reactions.
Synthesis and catalytic properties of 4-aryl-2,3-dihydro-4H-pyrimido[2,3-b]benzothiazoles for asymmetric acyl or carboxyl group transfer reactions.
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DOI：
10.1021/jo200984n
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发表时间：
2011-07
期刊：
影响因子：
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通讯作者：
Baby Viswambharan;Tatsuya Okimura;Satoko Suzuki;S. Okamoto
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文献类型：
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作者：
Baby Viswambharan;Tatsuya Okimura;Satoko Suzuki;S. Okamoto
合成了4-芳基-2，3-二氢-4H-嘧啶并[2，3-B]苯并噻唑（4-Ar-DHPB），并评价了它们在仲醇动力学拆分、Steglich重排及相关反应中的催化活性和选择性。4-芳基-DHPB在1-苯基乙醇的酰化动力学拆分中表现出较低的对映选择性。相反，他们催化的Steglich重排具有中等至优异的对映体选择性，证明远程立体控制的可能性，通过引入取代基在4-位的DHPB。
4-Aryl-2,3-dihydro-4H-pyrimido[2,3-b]benzothiazoles (4-Ar-DHPBs) were synthesized and their catalytic activity and selectivity in kinetic resolution of a secondary alcohol as well as in the Steglich rearrangement and related reactions were evaluated. 4-Aryl-DHPBs showed low enantioselectivity in the acylative kinetic resolution of 1-phenylethanol. Conversely, they catalyzed the Steglich rearrangement with moderate to excellent enantioselectivity, demonstrating the possibility for remote stereocontrol by introduction of a substituent at the 4-position of DHPB.