Organocatalytic Diastereoselective Dearomative [4+2] Cyclodimerization of In-situ Generated ortho-Quinone Methides

被引：3

作者：

Sahoo, Sushree Ranjan ^{[1
]}

Singh, Vinod K. ^{[1
]}

机构：

[1] Indian Inst Technol Kanpur, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 12卷 / 11期

关键词：

cyclodimerization; diastereoselective; organocatalytic; spiro-cycle; CARBON QUATERNARY STEREOCENTERS; CATALYTIC ASYMMETRIC REACTIONS; FRIEDEL-CRAFTS ALKYLATION; ENANTIOSELECTIVE SYNTHESIS; CHIRALITY TRANSFER; C-3; CARBON; CONSTRUCTION; REARRANGEMENT; CYCLOADDITION; NAPHTHOLS;

D O I：

10.1002/ajoc.202300390

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We disclose a catalytic, diastereoselective dearomative [4+2] cyclodimerization of in-situ generated naphthol-derived ortho-quinone methides for the synthesis of spiro-naphthalenones (having an all-carbon quaternary stereocenter). This methodology offers a wide range of spiro-naphthalenone compounds in high yield with excellent diastereoselectivity and regiospecificity. Moreover, in the process, a diastereomeric interconversion of the cyclo-adduct in the presence of NaBH4 was also observed.

引用

页数：6

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