Hydroxy Group-Directed Homolytic Hydrostannylation of Alkenols with Dibutylchlorostannane
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In homolytic hydrostannylation of allyl alcohol <B>1a</B> or homoallyl alcohol <B>1b</B>, dibutylchlorostannane (Bu<SUB>2</SUB>ClSnH) exhibited a much higher reactivity than tributylstannane (Bu<SUB>3</SUB>SnH). Competitive reaction of <B>1a</B> <I>vs</I>. 1-octene with Bu<SUB>2</SUB>ClSnH led to the selective formation of γ-stannylated alcohol <B>3a</B>. Hydrostannylation of 1,5-hexadien-3-ol (<B>8</B>) with Bu<SUB>2</SUB>ClSnH favored 1-stannylated product <B>9</B> over 6-stannylated product <B>10</B>, while the use of Bu<SUB>3</SUB>SnH decreased the regioselectivity.
- Chemistry Letters
Chemistry Letters 1999(7), 659-660, 1999-07-05
The Chemical Society of Japan