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Literature DB >> 14558801

A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction.

David A Evans¹, Daniel Seidel, Magnus Rueping, Hon Wai Lam, Jared T Shaw, C Wade Downey.

Abstract

A highly enantioselective, nitroaldol reaction catalyzed by a chiral Cu(II) bis(oxazoline) complex has been developed. The reaction scope includes both aromatic and aliphatic aldehydes (15 examples) affording products in good yields and enantioselectivities (87-94% ee). An X-ray structure of the catalyst has been provided along with a rationalization of the sense of asymmetric induction.

Entities: Chemical

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Year: 2003 PMID： 14558801 DOI： 10.1021/ja0373871

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

17 in total

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Journal: J Org Chem Date: 2017-08-14 Impact factor: 4.354

2. Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids.

Authors: Hongming Li; Baomin Wang; Li Deng
Journal: J Am Chem Soc Date: 2006-01-25 Impact factor: 15.419

3. Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers.

Authors: Jiajing Tan; Cheol-Hong Cheon; Hisashi Yamamoto
Journal: Angew Chem Int Ed Engl Date: 2012-07-23 Impact factor: 15.336

10. The Formation of Impossible Rings in Macrocyclooligomerizations for Cyclodepsipeptide Synthesis: The 18-from-12 Paradox.

Authors: Abigail N Smith; Jeffrey N Johnston
Journal: J Org Chem Date: 2021-06-07 Impact factor: 4.354

A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction.

1. Asymmetric Formal Synthesis of the Long-Acting DPP-4 Inhibitor Omarigliptin.

2. Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids.

3. Catalytic asymmetric Claisen rearrangement of enolphosphonates: construction of vicinal tertiary and all-carbon quaternary centers.

4. Chelation-assisted, copper(II)-acetate-accelerated azide-alkyne cycloaddition.

5. Crystallization-Enabled Henry Reactions: Stereoconvergent Construction of Fully Substituted [N]-Asymmetric Centers.

6. Coordination compounds based on 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid.

7. Enantioselective synthesis of α-oxy amides via Umpolung amide synthesis.

8. Catalytic enantioselective Henry reaction of α-keto esters, 2-acylpyridines and 2-acylpyridine N-oxides.

9. Enantioselective Synthesis of D-α-Amino Amides from Aliphatic Aldehydes.

10. The Formation of Impossible Rings in Macrocyclooligomerizations for Cyclodepsipeptide Synthesis: The 18-from-12 Paradox.