Diastereoselective 1,6-Addition of α-Phosphonyloxy Enolates to para-Quinone Methides

被引：20

作者：

Ali, Amjad ^{[1
]}

Jajoria, Raveena ^{[1
]}

Harit, Harish K. ^{[1
]}

Singh, Ravi P. ^{[1
]}

机构：

[1] Indian Inst Technol Delhi, Dept Chem, New Delhi 110016, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 08期

关键词：

FRIEDEL-CRAFTS REACTION; SPIROCYCLOPROPANATION REACTION; KETOESTERS; ISATINS;

D O I：

10.1021/acs.joc.2c00030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of alpha-ketoamide top-quinone methide initiated by dialkylphosphite in the presence of organic base 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU) is explored. Coupling of dialkylphosphites to alpha-ketoamides in the presence of a base follows[1,2]-phospha-Brook rearrangement, generating corresponding alpha-phosphonyloxy enolates that are subsequently seized byp-quinonemethides (p-QMs). The two-step one-pot 1,6-conjugate addition provides effective access to a series of isatin-incorporatedphosphate-bearing 1,6-adducts having two vicinal tertiary carbons with up to 90% yield and >20:1dr

引用

页码：5213 / 5228

页数：16

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