Stereoselective synthesis of alcohols, XXIII. Transfer of chirality on addition of (α‐chloroallyl)boronates to aldehydes | Zendy

Hoffmann Reinhard W. | Zendy; Landmann Bernd | Zendy

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Stereoselective synthesis of alcohols, XXIII. Transfer of chirality on addition of (α‐chloroallyl)boronates to aldehydes

Author(s) -

Hoffmann Reinhard W.,

Landmann Bernd

Publication year - 1986

Publication title -

chemische berichte

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.667

H-Index - 136

eISSN - 1099-0682

pISSN - 0009-2940

DOI - 10.1002/cber.19861190622

Subject(s) - chemistry , diastereomer , stereoselectivity , aldehyde , reagent , stereochemistry , chirality (physics) , selectivity , medicinal chemistry , organic chemistry , catalysis , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark

The preparation of the (α‐chloroallyl)boronate 4 of 92% e.e. is described. Its addition to achiral aldehydes resulted in the homoallyl alcohols 6 of 82–92% e.e. Cooperative diastereoface selectivity on addition of ent ‐ 4 to isopropylideneglyceraldehyde ( 22 ) gave the product 23 of high diastereomeric purity. Reagent control of stereoselectivity on addition of 4 to 22 resulted in 25 of 77% diastereomeric purity.

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