Process for producing allylic alcohols

Details Process for producing allylic alcohols Process for producing allylic alcohols

1990-05-29

1991-04-02

Siegel, Alan

Organic compounds -- part of the class 532-570 series

Organic compounds

Oxygen containing

568675, 568808, 568813, 568817, 568821, 568828, 568838, 568839, 568908, 5689095, 549347, 549350, 549357, 549362, 549430, 549445, 549510, 549512, C07C 4100, C07C 3334, C07C 3328, C07C 3506

Patent

active

050048430

ABSTRACT:
Process for preparing predominantly Z-substituted allylic alcohols of the formula: ##STR1## wherein R.sup.1 is a straight or branched C.sub.1 -C.sub.25 alkyl group optionally bearing at least one substituent and/or at least one unsaturated linkage and R.sup.2 is a hydrogen atom or a methyl group, which comprises reacting a vinyl epoxide of the formula: ##STR2## wherein R.sup.2 is as defined above with an organolithium compound of the formula above. More particularly, there is disclosed a process for R.sup.1 --Li wherein R.sup.1 is as defined above; particularly, process for preparing .alpha.-santalol of the formula: ##STR3## which comprises reacting 3-methyl-3,4-epoxybutene-1 with lithiomethyl-2,3-dimethyltricyclo[2.2.1.0.sup.2,6 ]heptane.

REFERENCES:
Aithie et al., Tetrahedron Letters 49, 4419-4420 (1975).
Anderson, J. Amer. Chem. Soc. 92, 4978-4979 (1970).
Herr et al., J. Amer. Chem. Soc. 92, 4979-4981 (1970).
J. of Am. Chem. Soc., 95, 957 (1973).
J. Am. Chem. Soc., 92, 226 (1970).
Tetrahedron Letters, 1975, 4419.
Aithie et al., Tetrahedron Letters, 1975, 4419.

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