Lewis Acid-Catalyzed Addition of Alkenylzirconocenes to Carbonyl Compounds: Remarkable Activity of Trimethylsilyl Triflate
ABSTRACT Addition of 1-pentadecenylzirconocene chloride to 2,3-O-cyclohexylidene-(R)-glyceraldehyde in CH 2 Cl 2 was best promoted by trimethylsilyl triflate (TMSOTf) to give the diastereomeric ANTI- and SYN-alcohols in 80% yield. TMSOTf also showed remarkable catalytic activity for the addition of...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2004-07, Vol.2004 (10), p.1566-1572 |
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| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | ABSTRACT
Addition of 1-pentadecenylzirconocene chloride to 2,3-O-cyclohexylidene-(R)-glyceraldehyde in CH
2
Cl
2
was best promoted by trimethylsilyl triflate (TMSOTf) to give the diastereomeric ANTI- and SYN-alcohols in 80% yield. TMSOTf also showed remarkable catalytic activity for the addition of 1(E)-alkenylzirconocenes to ketones, giving tertiary allylic alcohols in good yields. |
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| ISSN: | 0039-7881 1437-210X |
| DOI: | 10.1055/s-2004-829108 |