Tandem IBX‐Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ‐Diolcarbonate Aldehydes to ( E )‐γ‐Hydroxy‐α,β‐enals | Zendy

Kumari Anupama | Zendy; Gholap Sachin P. | Zendy; Fernandes Rodney A. | Zendy

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Tandem IBX‐Promoted Primary Alcohol Oxidation/Opening of Intermediate β,γ‐Diolcarbonate Aldehydes to ( E )‐γ‐Hydroxy‐α,β‐enals

Author(s) -

Kumari Anupama,

Gholap Sachin P.,

Fernandes Rodney A.

Publication year - 2019

Publication title -

chemistry – an asian journal

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.18

H-Index - 106

eISSN - 1861-471X

pISSN - 1861-4728

DOI - 10.1002/asia.201900421

Subject(s) - aldehyde , tandem , primary (astronomy) , alcohol , chemistry , stereoselectivity , alcohol oxidation , olefin fiber , primary alcohol , organic chemistry , catalysis , materials science , physics , astronomy , composite material

A tandem IBX‐promoted oxidation of primary alcohol to aldehyde and opening of intermediate β,γ‐diolcarbonate aldehyde to ( E )‐γ‐hydroxy‐α,β‐enal has been developed. Remarkably, the carbonate opening delivered exclusively ( E )‐olefin and no over‐oxidation of γ‐hydroxy was observed. The method developed has been extended to complete the stereoselective total synthesis of both ( S )‐ and ( R )‐coriolides and d ‐ xylo ‐ and d ‐ arabino ‐C‐20 guggultetrols.

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