[Fe(diene)(CO)3] complexes as a guide in stereocontrol. Applications to the asymmetric synthesis of natural products
[Fe(diene)(CO)3] complexes as a guide in stereocontrol. Applications to the asymmetric synthesis of natural products
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[Fe(二烯)(CO)3]配合物作为立体控制的指导。
DOI：
10.1039/cc9960002497
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发表时间：
1996
影响因子：
4.9
通讯作者：
Y. Takemoto
中科院分区：
文献类型：
--
作者：
C. Iwata;Y. Takemoto
本文描述了三羰基铁单元控制与相邻CX（X = O，N）双键亲核加成和通过η5阳离子中间体进行1，5亲核取代的区域和立体化学的能力。我们研究了无环[Fe（diene）（CO）3]配合物作为手性助剂用于天然产物不对称合成的潜力。利用Fe（diene）（CO）_3的立体定向能力和迁移性，实现了（+）和（-）-frontalin、羟基亚乙基二肽电子等排体、哌啶生物碱（SS 20846 A）和N-Boc-O-Me-（2 R，3S，5E，7 E）-2-氨基十四碳-5，7-二烯-3-醇的不对称合成。此外，我们开发了一种有效的合成手性双烯醛Fe（CO）3配合物的方法，这是一种通用的原料，用于不对称合成上述生物活性的天然产物。
The ability of iron tricarbonyl units to control the region- and stereo-chemistry of nucleophilic addition to a neighbouring CX (X = O, N) double bond and 1,5-nucleophilic substitution via a η5-cation intermediate are described. We investigated the potential of acyclic [Fe(diene)(CO)3] complexes as chiral auxiliaries for the asymmetric synthesis of natural products. The asymmetric syntheses of (+) and (–)-frontalin, a hydroxyethylidene dipeptide isostere, a piperidine alkaloid (SS20846A), and N-Boc-O-Me-(2R,3S,5E,7E)-2-aminotetradeca- 5,7-dien-3-ol were achieved by using the stereodirecting ability and mobility of the Fe(diene)(CO)3 group. In addion, we developed an efficient method for synthesizing chiral dienal Fe(CO)3 complexes, which are versatile starting materials for the asymmetric synthesis of the biologically active natural products described above.