Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral N -Sulfonyl Imines
Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral N -Sulfonyl Imines
复制标题
前手性亲核烯烃与 α-手性 N-磺酰亚胺的非对映选择性加成
DOI：
10.1021/acs.orglett.1c04219
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发表时间：
2022
期刊：
影响因子：
5.2
通讯作者：
Shaw, Jared T.
中科院分区：
文献类型：
--
作者：
Gutierrez, David A.;Fettinger, James;Houk, K. N.;Ando, Kaori;Shaw, Jared T.
描述了路易斯酸促进前手性E-和Z-烯丙基亲核试剂与手性α-烷氧基N-甲苯磺酰亚胺的加成反应。烯烃几何结构选择性地转移到新形成的碳-碳键上，从而对所得 2-烷氧基-3-N-甲苯磺酰基-4-烷基-5-己烯产物的 C1、C2 和 C3 进行立体化学控制。还提出了阐明高选择性的计算分析。该方法用于合成黄皮酰胺的两种天然异构体。
The Lewis-acid-promoted addition of prochiralE- andZ-allyl nucleophiles to chiral α-alkoxyN-tosyl imines is described. Alkene geometry is selectively transferred to the newly formed carbon–carbon bond, resulting in stereochemical control of C1, C2, and C3 of the resulting 2-alkoxy-3-N-tosyl-4-alkyl-5-hexene products. A computational analysis to elucidate the high selectivity is also presented. This methodology was employed in the synthesis of two naturally occurring isomers of clausenamide.