A new organocatalyzed Michael-Michael cascade reaction generates highly substituted fused carbocycles

Patrick G. McGarraugh; Stacey E. Brenner

doi:10.1021/ol9024293

A new organocatalyzed Michael-Michael cascade reaction generates highly substituted fused carbocycles

Patrick G. McGarraugh, Stacey E. Brenner

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

Abstract

[Chemical Equation Presented] While β-ketoesters are useful Michael donors, they were previously ineffective in Michael-Michael cascade reactions using αβ-unsaturated aldehydes in conjunction with diphenylprolinol silyl ether organocatalysts. However, through rational modification of substrates and manipulation of the catalytic cycle, we developed an efficient Michael-Michael cascade reaction using β-ketoesters of type 9. In this transformation, highly substituted fused carbocycles are generated In a single step In up to 87% yield and 99% ee.

Original language	English (US)
Pages (from-to)	5654-5657
Number of pages	4
Journal	Organic letters
Volume	11
Issue number	24
DOIs	https://doi.org/10.1021/ol9024293
State	Published - Dec 17 2009
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol9024293

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abstract = "[Chemical Equation Presented] While β-ketoesters are useful Michael donors, they were previously ineffective in Michael-Michael cascade reactions using αβ-unsaturated aldehydes in conjunction with diphenylprolinol silyl ether organocatalysts. However, through rational modification of substrates and manipulation of the catalytic cycle, we developed an efficient Michael-Michael cascade reaction using β-ketoesters of type 9. In this transformation, highly substituted fused carbocycles are generated In a single step In up to 87% yield and 99% ee.",

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year = "2009",

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N2 - [Chemical Equation Presented] While β-ketoesters are useful Michael donors, they were previously ineffective in Michael-Michael cascade reactions using αβ-unsaturated aldehydes in conjunction with diphenylprolinol silyl ether organocatalysts. However, through rational modification of substrates and manipulation of the catalytic cycle, we developed an efficient Michael-Michael cascade reaction using β-ketoesters of type 9. In this transformation, highly substituted fused carbocycles are generated In a single step In up to 87% yield and 99% ee.

AB - [Chemical Equation Presented] While β-ketoesters are useful Michael donors, they were previously ineffective in Michael-Michael cascade reactions using αβ-unsaturated aldehydes in conjunction with diphenylprolinol silyl ether organocatalysts. However, through rational modification of substrates and manipulation of the catalytic cycle, we developed an efficient Michael-Michael cascade reaction using β-ketoesters of type 9. In this transformation, highly substituted fused carbocycles are generated In a single step In up to 87% yield and 99% ee.

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A new organocatalyzed Michael-Michael cascade reaction generates highly substituted fused carbocycles

Abstract

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