Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase.
Enantioselective direct Mannich-type reactions of 2-benzylpyridine N-oxides catalyzed by chiral bis(guanidino)iminophosphorane organosuperbase.
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DOI：
10.1039/c8sc00808f
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发表时间：
2018-05-14
期刊：
影响因子：
8.4
通讯作者：
Terada M
中科院分区：
文献类型：
--
作者：
Hu Q;Kondoh A;Terada M
具有酸性α-质子较少的2-苄基吡啶n -氧化物首次被用于Brønsted碱催化的对映选择性加成反应中。具有酸性α-质子较少的2-苄基吡啶n -氧化物首次被用于Brønsted碱催化的对映选择性加成反应中。手性双胍亚磷烷能够克服原亲核试剂酸性低的固有问题，与N-Boc亚胺建立非映对和对映选择性直接曼尼奇型反应。对照实验表明，基底的n -氧化物部分在实现高立体选择性中起着关键作用。
2-Benzylpyridine N-oxides possessing less acidic α-protons were utilized as pronucleophiles for the first time in enantioselective addition reactions under Brønsted base catalysis. 2-Benzylpyridine N-oxides possessing less acidic α-protons were utilized as pronucleophiles for the first time in enantioselective addition reactions under Brønsted base catalysis. A chiral bis(guanidino)iminophosphorane was able to overcome the inherent issue of low acidity of the pronucleophiles, establishing the diastereo- and enantioselective direct Mannich-type reaction with N-Boc imines. The control experiments indicated that the N-oxide moiety of the substrates played a critical role in achieving the high stereoselectivity.
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