Boron-based pronucleophiles in catalytic (asymmetric) C(sp3)–allyl cross-couplings
Boron-based pronucleophiles in catalytic (asymmetric) C(sp3)–allyl cross-couplings
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DOI：
10.1351/pac-con-12-05-01
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发表时间：
2012-08
影响因子：
1.8
通讯作者：
U. Schneider;Yiyong Huang;A. Chakrabarti;H. T. Dao;N. Morita;S. Kobayashi
中科院分区：
文献类型：
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作者：
U. Schneider;Yiyong Huang;A. Chakrabarti;H. T. Dao;N. Morita;S. Kobayashi
发现烯丙基和丙二烯基硼酸酯或硼烷在与C（sp3）亲电试剂如O，O-缩醛和N，O-缩醛或醚和碳水化合物的催化C-C键形成中是合适的亲核试剂。In（I）triflate最有效地催化这些转化。重要的是，通过使用由氯化铟（I）和手性银2，2 '-二羟基-1，1'-联萘（BINOL）-磷酸酯组成的催化剂体系，开发了手性反阴离子导向的催化N，O-氨基醛的不对称烯丙基化和联烯基化。
Allylic and allenyl boronates or boranes were uncovered as suitable pronucleophiles in catalytic C–C bond formations with C(sp3) electrophiles such as O,O-acetals and N,O-aminals or ethers and carbohydrates. These transformations were most efficiently catalyzed by In(I) triflate. Importantly, chiral counteranion-directed, catalytic asymmetric allylation and allenylation of N,O-aminals was developed by employing a catalyst system composed of In(I) chloride and a chiral silver 2,2'-dihydroxy-1,1'-binaphthalene (BINOL)-phosphate.