265661-36-7Relevant academic research and scientific papers
Straight and versatile synthesis of substituted perhydrofuro[2,3-b]pyrans from 2-chloromethyl-3-(2-methoxyethoxy)propene
Alonso, Francisco,Lorenzo, Emilio,Meléndez, Jaisiel,Yus, Miguel
, p. 5199 - 5208 (2003)
The reaction of 2-chloromethyl-3-(2-methoxyethoxy)propene with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E1=R1R2CO) in THF at -78 to 0°C, followed by the addition of an epoxide [E2=R3R4C(O)CHR5] at 0 to 20°C leads, after hydrolysis, to the expected methylidenic diols. These diols when subjected to successive hydroboration-oxidation and further oxidation, spontaneous cyclization occurs to furnish a series of differently substituted perhydrofuro[2,3-b]pyrans.
Regioselective synthesis of 1,7-dioxaspiro[4.4]nonanes from a trimethylenemethane dianion synthon
Alonso, Francisco,Dacunha, Bruno,Meléndez, Jaisiel,Yus, Miguel
, p. 3437 - 3450 (2005)
2-Chloromethyl-3-(2-methoxyethoxy)prop-1-ene behaves as a versatile trimethylenemethane dianion synthon, precursor of a variety of methylidenic diols obtained by DTBB-catalysed lithiation in the presence of a carbonyl compound (E1=R1R2CO) in THF at -78 to 0°C, followed by the addition of an epoxide [E2=R3R 4C(O)CHR5] at 0 to 20°C and final hydrolysis. These diols undergo double intramolecular iodoetherification in the presence of iodine and silver(I) oxide in THF or dioxane-water, to give the corresponding 1,7-dioxaspiro[4.4]nonanes, which can be easily oxidised to a variety of 1,7-dioxaspiro[4.4]nonan-6-ones. These skeletons are present in a wide series of natural products.
Straightforward synthesis of 1,7-dioxaspiro[4.4]nonanes
Alonso, Francisco,Meléndez, Jaisiel,Yus, Miguel
, p. 1717 - 1720 (2004)
The reaction of 2-chloromethyl-3-(2-methoxyethoxy)prop-1-ene with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E1=R1R2CO) in THF at -78 to 0°C, followed by the addition of an epoxide [E 2=R3R4C(O)CHR5] at 0 to 20deg;C leads, after hydrolysis, to the expected methylidenic diols. These diols, in the presence of iodine and silver(I) oxide in dioxane-water, undergo double intramolecular iodoetherification to give the corresponding 1,7-dioxaspiro[4.4] nonanes, which in addition can be easily oxidised to a variety of 1,7-dioxaspiro[4.4]nonan-6-ones.
Substituted perhydrofuropyrans: Easy preparation from 2-chloromethyl-3- (2-methoxyethoxy)propene through 3-methylene-1,6-diols
Lorenzo, Emilio,Alonso, Francisco,Yus, Miguel
, p. 1661 - 1665 (2007/10/03)
The reaction of 2-chloromethyl-3-(2-methoxyethoxy)prop-1-ene (1) with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of a carbonyl compound (E1=R1R2CO) in THF at -78 to 0°C, followed by treatment with an epoxide [E2=R3R4C(O)CHR5] at 0 to 20°C leads, after hydrolysis, to the expected unsaturated diols 2. When some compounds 2 (2e-h) are successively hydroborated (BH3 · THF) and oxidised (33% H2O2 and then PCC), the expected perhydrofuropyrans 3e-h are isolated directly. (C) 2000 Elsevier Science Ltd.
