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Gold(I)-Catalyzed Stereoselective Cyclization of 1,3-Enyne Aldehydes by 1,3-Acyloxy Migration/Nazarov/Aldol Cascade

10 June 2019, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Stereoselective synthesis of bicyclo[3.3.0]octenones from chiral 1,3 enyne aldehydes bearing propargylic acetates is described. The method is based on a Au(I)-catalyzed domino sequence with concomitant transfer of chirality involving 1,3-acyloxy migration followed by Nazarov cyclization and an unprecedented aldol addition. The method furnishes densely functionalized bicyclic structures in high yields, up to 97% ee, and good diastereoselectivity.

Keywords

Gold
Catalysis
Methodology
Pentalenes
Cascade

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Version History

Jun 10, 2019 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.8247803.v1
D O I: 10.26434/chemrxiv.8247803.v1 [opens in a new tab]

Funding

ETH Zurich
Stipendienfonds Schweizerische Chemische Industrie (SSCI)

Author’s competing interest statement

No Conflict of Interest

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