Enantioselective Annulation Reactions Enabled by Chiral Lithium Amides as Traceless Auxiliaries

Functionalized multimembered carbocyclic compounds are synthetically challenging scaffolds found in numerous pharmaceuticals and natural products. Herein, we describe a stereoselective and operationally straightforward method to form such carbocyclic compounds via a Michael addition-cyclization cascade. This method is effective in forming three or more contiguous stereocenters with high enantio- and diastereocontrol directly from α-substituted arylacetic acids with chiral lithium amides (CLAs) as traceless stereodirecting auxiliaries.

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Publication Details

Journal
Organic Letters
Published
2025-02-04
DOI
https://doi.org/10.1021/acs.orglett.4c04870
Citations
3
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
2.81

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article

Enantioselective Annulation Reactions Enabled by Chiral Lithium Amides as Traceless Auxiliaries

Leroy Lu, Armen Zakarian, Kai Yu, Jessica Park et al.
3 citations
Organic Letters
Asymmetric Synthesis and Catalysis
2.81
article

Enantioselective Annulation Reactions Enabled by Chiral Lithium Amides as Traceless Auxiliaries

Leroy Lu, Armen Zakarian, Kai Yu, Jessica Park, Peng Pan, Lev N. Sepetov, Lauren Purcell
article en
3 citations

Abstract

Functionalized multimembered carbocyclic compounds are synthetically challenging scaffolds found in numerous pharmaceuticals and natural products. Herein, we describe a stereoselective and operationally straightforward method to form such carbocyclic compounds via a Michael addition-cyclization cascade. This method is effective in forming three or more contiguous stereocenters with high enantio- and diastereocontrol directly from α-substituted arylacetic acids with chiral lithium amides (CLAs) as traceless stereodirecting auxiliaries.

Organic LettersVol. 27(6)
University of California, Santa Barbara (US), University of California System (US)
Division of Chemistry
Openalex Percentile: Top 12%
Asymmetric Synthesis and Catalysis
2.81
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Enantioselective Annulation Reactions Enabled by Chiral Lithium Amides as Traceless Auxiliaries — Leroy Lu, Armen Zakarian, et al. · Organic Letters (2025) | TGRS Research Map | TGRS