Reductive coupling of allenoates with aldehydes catalyzed by halogenotin hydride

Itaru Suzuki; Yu-Ya Hamada; Yuki Uji; Ikuya Shibata

doi:10.1039/d2ob01096h

Reductive coupling of allenoates with aldehydes catalyzed by halogenotin hydride

Org Biomol Chem. 2022 Jul 13;20(27):5402-5405. doi: 10.1039/d2ob01096h.

Authors

Itaru Suzuki¹, Yu-Ya Hamada², Yuki Uji², Ikuya Shibata^{1

2}

Affiliations

¹ Research Center for Environmental Preservation, Osaka University, 2-4 Yamadaoka, Suita, Osaka 565-0871, Japan. shibata@epc.osaka-u.ac.jp.
² Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871, Japan.

PMID: 35786735
DOI: 10.1039/d2ob01096h

Abstract

Hydrostannylation of allenoate 1 with halogenotin hydride (Bu₂SnClH) was developed to give allylic stannane (I), which then could react with aldehyde 2. The same coupling gave allylic alcohol 3 under reductive conditions in the presence of a silane and a catalytic amount of Bu₂SnClH. This catalytic protocol was applied to the synthesis of lactone 4. The resultant products 3 and 4 were subjected to oxidative conditions to provide oxacycles 5 and 6, respectively.

MeSH terms

Aldehydes*
Catalysis
Molecular Structure
Oxidation-Reduction
Silanes*

Substances

Aldehydes
Silanes