Redox-Neutral 1,3-Diol Synthesis by Base-Promoted Diastereoselective Alcohol–Aldolization | Zendy

Na Shao | Zendy; Jean Rodríguez | Zendy; Adrien Quintard | Zendy

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Redox-Neutral 1,3-Diol Synthesis by Base-Promoted Diastereoselective Alcohol–Aldolization

Author(s) -

Na Shao,

Jean Rodríguez,

Adrien Quintard

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02536

Subject(s) - chemistry , redox , base (topology) , diol , alcohol , combinatorial chemistry , organic chemistry , stereochemistry , mathematical analysis , mathematics

In order to prepare more efficiently key 1,3-diol fragments, we have devised a base-promoted redox-neutral condensation of ketones with alcohols. This diastereoselective alcohol-aldolization enables bypassing the classical oxidation and reduction steps necessary for the preparation of this crucial backbone by an overall redox-neutral formal borrowing hydrogen process. The starting alcohols constitute both the precursors of the in situ generated reactive aldehydes and the hydride source necessary for the chemoselective reduction of the aldol adduct intermediates.

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