Catalytic asymmetric Pictet-Spengler reactions via sulfenyliminium ions
Catalytic asymmetric Pictet-Spengler reactions via sulfenyliminium ions
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DOI：
10.1002/anie.200701808
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发表时间：
2007-01-01
影响因子：
16.6
通讯作者：
Hiemstra, Henk
中科院分区：
文献类型：
--
作者：
Wanner, Martin J.;van der Haas, Richard N. S.;Hiemstra, Henk
意义：作者报道了色胺通过亚磺酰亚胺离子的催化不对称Pictet-Spengler反应。手性磷酸1是该反应的最佳催化剂，并且色胺底物上的N-三苯甲基硫基取代基被发现对于实现高的对映选择性和转化率是必不可少的。3，5-二（叔丁基）-4-羟基甲苯（BHT）作为自由基清除剂，防止产物分解。作者在酸性条件下一锅法除去了硫基。当催化剂用量为5mol%时，不同醛的产率可达77-90%，对映选择性为65：35 - 93：7。
Significance: The authors report a catalytic asymmetric Pictet–Spengler reaction of tryptamine via a sulfenyliminium ion. Chiral phosphoric acid 1 was the best catalyst for this reaction and the N-tritylsulfenyl substituent on the tryptamine substrate was found to be essential for achieving high enantioselectivity and conversion. 3, 5-Di (tert-butyl)-4-hydroxytoluene (BHT) acts as radical scavenger and prevents the decomposition of the product. The authors have removed the sulfenyl group under acidic conditions in one pot. With 5 mol% of catalyst 1 good to excellent yields (77–90%) and moderate to high enantioselectivities (er= 65: 35 to 93: 7) are obtained for different aldehydes.