Concepedia

Asymmetric Formal [3 + 2] Cycloaddition Reaction of Succinaldehyde via Diarylprolinol-mediated Domino Aldol–Acetalization Reaction for the Construction of Tetrahydrofuran

Yujiro Hayashi, Kentaro Nishino, Itaru Sato

Chemistry Letters · 2013 · 15 citations · 20 references

DOI

Concepts

Abstract

Abstract Highly enantioselective synthesis of tetrahydrofurans was accomplished via a formal [3 + 2] cycloaddition reaction of succinaldehyde, which acts as a three-carbon unit. The reaction consists of the domino reaction of the diarylprolinol-mediated aldol reaction of succinaldehyde followed by an intramolecular acetalization reaction.

References

20

Diphenylprolinol Silyl Ethers as Efficient Organocatalysts for the Asymmetric Michael Reaction of Aldehydes and Nitroalkenes

Yujiro Hayashi, Hiroaki Gotoh, Takaaki Hayashi et al. · Angewandte Chemie International Edition · 2005 · 1.2K citations

, , +14

Enantioselective Organocatalyzed α Sulfenylation of Aldehydes

Mauro Marigo, Tobias C. Wabnitz, Doris Fielenbach et al. · Angewandte Chemie International Edition · 2005 · 947 citations · Full text

, , +9

Organocatalytic Asymmetric Domino Reactions: A Cascade Consisting of a Michael Addition and an Aldehyde α‐Alkylation

Dieter Enders, Chuan Wang, Jan W. Bats · Angewandte Chemie International Edition · 2008 · 217 citations

, , +13

Asymmetric Aldol Reaction of Acetaldehyde and Isatin Derivatives for the Total Syntheses of <i>ent</i>-Convolutamydine E and CPC-1 and a Half Fragment of Madindoline A and B

Takahiko Itoh, Hayato Ishikawa, Yujiro Hayashi · Organic Letters · 2009 · 209 citations

, , +9

A Diarylprolinol in an Asymmetric, Catalytic, and Direct Crossed‐Aldol Reaction of Acetaldehyde

Yujiro Hayashi, Seiji Aratake, Hayato Ishikawa · Angewandte Chemie International Edition · 2008 · 206 citations