Enantioselective α-Amination Enabled by a BINAM-Derived Phase-Transfer Catalyst.
Enantioselective α-Amination Enabled by a BINAM-Derived Phase-Transfer Catalyst.
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DOI：
10.1039/c4sc02494j
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发表时间：
2015-01-01
期刊：
影响因子：
8.4
通讯作者：
Toste FD
中科院分区：
文献类型：
--
作者：
Nelson HM;Patel JS;Shunatona HP;Toste FD
通过BINAM衍生的磷酸与芳基重氮盐的相转移实现了羰基衍生物的对映选择性胺化。利用芳香重氮阳离子的手性阴离子相转移实现了羰基化合物的高对映选择性α-胺化反应。一个广泛的茚满酮和苯并环庚酮衍生的底物是服从这一战略。获得高水平的对映体选择性的关键是使用BINAM衍生的磷酸。通过将二氮烯产物容易地转化为有价值的α-氨基酸衍生物，证明了这种转化的实用性。
The enantioselective amination of carbonyl derivatives is achieved via phase-transfer of aryldiazonium salts by BINAM-derived phosphoric acids. Chiral anion phase-transfer of aryldiazonium cations was utilized to achieve highly enantioselective α-amination of carbonyl compounds. A broad scope of indanone- and benzosuberone-derived substrates was amenable to this strategy. Critical to obtaining high levels of enantioselectivity was the use of BINAM-derived phosphoric acids. The utility of this transformation was demonstrated through facile conversion of diazene products to valuable α-amino acid derivatives.