Mixed metal bases as promoters of 1,4-eliminations
1990
Abstract
When treated with the LIDAKOR mixt., allyl type ethers very readily undergo 1,4-elimination to afford conjugated dienes (E)-H2C:CHCH:CH(CH2)4Me, H2C:C(:CH2)CH2CH2CH:CMe2, H2C:CHCH:CHOMe. In typical cases, the reaction is brought about stereo- and regioselectively, e.g., (E)-H2C:CHCH:CH(CH2)4Me and H2C:C(:CH2)CH2CH2CH:CMe2). Under suitable conditions, lithium dimethylamide or even lithium diisopropylamide adds to the dienes generated in situ thus leading to a variety of new allyl amines Me2C:CHCH2CH2C(CH2NMe2):CHMe, Me2CHCH2CH2CH:CMeCH:CHNMe2, and (Z)-MeCH:CHCH2N(CHMe2)2. [on SciFinder (R)]
Details
Title
Mixed metal bases as promoters of 1,4-eliminations
Author(s)
Margot, Christian ; Matsuda, Hiroyuki ; Schlosser, Manfred
Published in
Tetrahedron
Volume
46
Issue
7
Pages
2425-2430
Date
1990
ISSN
0040-4020
Keywords
Addition reaction (of dialkylamides to alkadienes); Regiochemistry; Stereochemistry (of elimination of methanol and allyl ethers); Ethers Role: RCT (Reactant); RACT (Reactant or reagent) (allyl; elimination reaction of; with mixed metal bases); Alkadien; LIDAKOR elimination allyl ether; regioselectivity elimination allyl ether; stereoselectivity elimination allyl ether; base mixed metal elimination allyl ether; diene conjugated prepn addn amide; amine allyl
Note
CAN 113:115588
30-10
Terpenes and Terpenoids
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
34266-16-5P (2,4-Nonadiene) Role: FORM (Formation, nonpreparative), PREP (Preparation) (formation of, during mixed metal base-induced elimination of methanol from methoxynonene); 40930-20-9 Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation and addn. of dimethylamide to); 124-40-3 Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation and reaction of, with alkadienes); 60763-44-2 (Linalool methyl ether) Role: RCT (Reactant), RACT (Reactant or reagent) (methoxide elimination-dimethylamine addn. to); 2565-82-4 (Geraniol methyl ether); 2565-83-5 (Nerol methyl ether); 22805-71-6 ((E)-1,4-Dimethoxy-2-butene); 41649-14-3 ((Z)-1,4-Dimethoxy-2-butene); 129058-88-4 ((Z)-1-Methoxy-2-nonene) Role: RCT (Reactant), RACT (Reactant or reagent) (mixed metal base-induced elimination of methanol from); 3585-33-9P (Lithium dimethylamide) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and addn. of, to alkadienes); 41097-73-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, for THF); 59121-19-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced addn. dimethylamide to linalool Me ether); 129058-87-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced addn. of dimethylamide to methylpentadienol); 51768-88-8P; 53652-01-0P; 76027-12-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced addn. of dimethylamide to myrcene); 10034-09-0P; 19774-38-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced elimination reaction of dimethoxybutene); 56700-77-7P ((E)-1,3-Nonadiene) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced elimination reaction of methoxynonane); 123-35-3P (Myrcene) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced elimination reaction of nerol and geraniol ethers); 106-99-0 (1,3-Butadiene); 117421-76-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with lithium diisopropylamide-tert-butoxide); 109-99-9 (Tetrahydrofuran) Role: RCT (Reactant), RACT (Reactant or reagent) (ring cleavage-diisopropylamide addn. to); 16302-35-5 Role: RCT (Reactant), RACT (Reactant or reagent) (ring opening and addn. of dimethylamide to)
30-10
Terpenes and Terpenoids
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
written in English.
34266-16-5P (2,4-Nonadiene) Role: FORM (Formation, nonpreparative), PREP (Preparation) (formation of, during mixed metal base-induced elimination of methanol from methoxynonene); 40930-20-9 Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation and addn. of dimethylamide to); 124-40-3 Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation and reaction of, with alkadienes); 60763-44-2 (Linalool methyl ether) Role: RCT (Reactant), RACT (Reactant or reagent) (methoxide elimination-dimethylamine addn. to); 2565-82-4 (Geraniol methyl ether); 2565-83-5 (Nerol methyl ether); 22805-71-6 ((E)-1,4-Dimethoxy-2-butene); 41649-14-3 ((Z)-1,4-Dimethoxy-2-butene); 129058-88-4 ((Z)-1-Methoxy-2-nonene) Role: RCT (Reactant), RACT (Reactant or reagent) (mixed metal base-induced elimination of methanol from); 3585-33-9P (Lithium dimethylamide) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and addn. of, to alkadienes); 41097-73-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, for THF); 59121-19-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced addn. dimethylamide to linalool Me ether); 129058-87-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced addn. of dimethylamide to methylpentadienol); 51768-88-8P; 53652-01-0P; 76027-12-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced addn. of dimethylamide to myrcene); 10034-09-0P; 19774-38-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced elimination reaction of dimethoxybutene); 56700-77-7P ((E)-1,3-Nonadiene) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced elimination reaction of methoxynonane); 123-35-3P (Myrcene) Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, via mixed metal base-induced elimination reaction of nerol and geraniol ethers); 106-99-0 (1,3-Butadiene); 117421-76-8 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with lithium diisopropylamide-tert-butoxide); 109-99-9 (Tetrahydrofuran) Role: RCT (Reactant), RACT (Reactant or reagent) (ring cleavage-diisopropylamide addn. to); 16302-35-5 Role: RCT (Reactant), RACT (Reactant or reagent) (ring opening and addn. of dimethylamide to)
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Record creation date
2006-03-03