Lewis Acid-Catalyzed Addition of Alkenylzirconocenes to Carbonyl Compounds: Remarkable Activity of Trimethylsilyl Triflate

Teiichi Murakami; Kiyotaka Furusawa

doi:10.1055/s-2004-829108

PAPER

Lewis Acid-Catalyzed Addition of Alkenylzirconocenes to Carbonyl Compounds: Remarkable Activity of Trimethylsilyl Triflate

Teiichi Murakami*, Kiyotaka Furusawa
National Institute of Advanced Industrial Science and Technology (AIST), Tsukuba Central 5, Tsukuba, Ibaraki 305-8565, Japan
Fax: +81(29)8614487; e-Mail: t-murakami@aist.go.jp;

Abstract

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Abstract

Addition of 1-pentadecenylzirconocene chloride to 2,3-O-cyclohexylidene-(R)-glyceraldehyde in CH₂Cl₂ 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.

Key words

addition reactions - stereoselectivity - Lewis acids - alkenylation - hydrozirconation

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