Diastereoselective Additions of Chiral Vinylzinc Reagents to α-Chiral Aldehydes

Diastereoselective Additions of Chiral Vinylzinc Reagents to α-Chiral Aldehydes

Additions of vinylic zinc bromide reagents to α-chiral aldehydes (R1 = CH2OTBS, R2 = Me; R1 = Me, R2 = OTBS) in the presence of lithiated (+)- or (−)-N-methylephedrine proceed with predominant reagent control to afford anti or syn adducts stereoselectively, except when the aldehydes possess an alkox...

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Veröffentlicht in:Organic letters 2004-02, Vol.6 (3), p.445-448
Hauptverfasser: Marshall, James A, Eidam, Patrick
Format: Artikel
Sprache:eng
Schlagworte:
Aldehydes - chemistry
Ephedrine - analogs & derivatives
Ephedrine - chemistry
Lithium - chemistry
Magnesium - chemistry
Molecular Structure
Stereoisomerism
Vinyl Compounds - chemistry
Zinc - chemistry
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Zusammenfassung:Additions of vinylic zinc bromide reagents to α-chiral aldehydes (R1 = CH2OTBS, R2 = Me; R1 = Me, R2 = OTBS) in the presence of lithiated (+)- or (−)-N-methylephedrine proceed with predominant reagent control to afford anti or syn adducts stereoselectively, except when the aldehydes possess an alkoxy substituent at the α- or β-positions (R1 = Me, R2 = OBn; R1 = CH2OBn, R2 = Me), in which case chelation-controlled adducts predominate.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0363568