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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.