Facile isomerization of oxiranes to allyl alcohols by mixed metal bases

The mixt. of LiN(CHMe2)2 and KOCMe3 (LIDAKOR reagent) promotes smooth ring opening of oxiranes to afford allyl alcs. with good to excellent yields. Internal epoxyalkanes and large-sized epoxycycloalkanes give preferentially or exclusively (E)-alkenols. The regio- and stereochem. of the ring-opening reaction are essentially the consequence of syn-periplanar elimination mechanisms. [on SciFinder (R)]


Published in:
Tetrahedron, 46, 7, 2401-10
Year:
1990
Keywords:
Note:
CAN 113:190776
24-1
Alicyclic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4020
written in English.
3123-80-6P ((Z)-3-Octen-5-ol); 5665-82-7P (2-Ethyl-1-penten-3-ol); 130001-56-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, by ring opening of epoxide with base); 822-67-3P (2-Cyclohexen-1-ol); 2616-99-1P ((E)-3-Octen-5-ol); 3212-60-0P (2-Cyclopenten-1-ol); 4096-38-2P (2-Cyclohepten-1-ol); 4798-44-1P (1-Hexen-3-ol); 6221-49-4P ((E)-2-Cyclododecen-1-ol); 14390-23-9P (cis-2-Cyclooctene) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, by ring opening of epoxide with lithium diisopropylimide-potassium butoxide); 865-47-4 (Potassium tert-butoxide) Role: RCT (Reactant), RACT (Reactant or reagent) (reagent contg. lithium diisopropylamide and, for stereoselective ring opening of epoxides, allylic alcs. from); 4111-54-0 Role: RCT (Reactant), RACT (Reactant or reagent) (reagent, for stereoselective ring opening of epoxides, allylic alcs. from); 1439-06-1; 1689-70-9 Role: RCT (Reactant), RACT (Reactant or reagent) (ring opening of, with lithium diiospropylimide-potassium butoxide, stereochem. of); 285-67-6 (Cyclopentene oxide); 286-20-4 (Cyclohexene oxide); 286-45-3 (Cycloheptene oxide); 4925-71-7 (cis-Cyclooctene oxide) Role: RCT (Reactant), RACT (Reactant or reagent) (ring opening of, with lithium diisopropylamide-potassium butoxide, allylic alc. from); 1502-29-0 (cis-Cyclododecene oxide); 4683-60-7 (trans-Cyclododecene oxide) Role: RCT (Reactant), RACT (Reactant or reagent) (ring opening of, with lithium diisopropylamide-potassium butoxide, allylic alc. from stereoselective); 6124-90-9 (cis-2-Methyl-3-propyloxirane); 6124-91-0 (trans-2-Methyl-3-propyloxirane) Role: RCT (Reactant), RACT (Reactant or reagent) (ring opening of, with lithium diisopropylamide-potassium butoxide, regiochem. of); 130001-57-9 (trans-2,3-Diethyl-2-methyloxirane); 130001-58-0 (cis-2,3-Diethyl-2-methyloxirane) Role: RCT (Reactant), RACT (Reactant or reagent) (ring opening of, with lithium diisopropylimide-potassium butoxide, regio- and stereochem. of)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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