Construction of Functionalized Carbocycles Having Contiguous Tertiary Carbinol and All‐Carbon Stereogenic Centers
Construction of Functionalized Carbocycles Having Contiguous Tertiary Carbinol and All‐Carbon Stereogenic Centers
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DOI：
10.1002/ejoc.201201382
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发表时间：
2013-04
影响因子：
2.8
通讯作者：
C. Reddy;S. Babu;N. Aslam;V. Rajkumar
中科院分区：
文献类型：
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作者：
C. Reddy;S. Babu;N. Aslam;V. Rajkumar
据报道，一种高度立体选择性的方案用于定制功能化碳环结构单元（β-羟基酯）和双环内酯，其立体阵列包含连续的叔甲醇和全碳立体中心。提出了烯丙基和炔丙基铟对受阻α,α-二取代环烷酮的有效不对称诱导和非对映选择性加成。通过单晶 X 射线晶体结构分析明确建立了代表性产物的立体化学，并提出了一条合理的反应途径来支持高非立体选择性。
A highly stereoselective protocol is reported for customizing functionalized carbocyclic building blocks (β-hydroxy esters) and bicyclic lactones with a stereoarray that contains contiguous tertiary carbinol and all-carbon stereocenters. The efficient asymmetric induction and diastereofacial selective addition of allyl and propargyl indiums to hindered α,α-disubstituted cycloalkanones is presented. The stereochemistry of representative products was unequivocally established from single-crystal X-ray crystal structure analyses, and a plausible reaction pathway was proposed to support the high diastereofacial selectivity.