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2004
Alcohols
Q 0230
47- 073
Direct Preparation of Allylic Indium(III) Reagents from Allylic Alcohols via a
Reductive Transmetalation of π-Allylnickel(II) with Indium(I) Iodide. — Treatment of allylic alcohols with Ni(0) leads to π-allylnickel intermediates which in the
presence of InI are transformed into allylindium reagents. The latter smoothly react
with carbonyl compounds to afford homoallylic alcohols. Allylic alcohols bearing
small substituents generally leads to branched homoallylic alcohols with syn selectivity
irrespective of the C=C double bond geometry. Allylic alcohols having bulky substituents mainly yields the corresponding anti isomers. Under these conditions tandem coupling is possible giving the diols (XVII) and/or (XVIII). — (HIRASHITA, T.;
KAMBE, S.; TSUJI, H.; OMORI, H.; ARAKI*, S.; J. Org. Chem. 69 (2004) 15,
5054-5059; Nagoya Inst. Technol., Omohi Coll., Grad. Sch. Eng., Showa, Nagoya 466,
Japan; Eng.) — Jannicke
2004
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