Reaction of dimethoxycarbene-DMAD zwitterion with 1,2-diones and anhydrides: a novel synthesis of highly substituted dihydrofurans and spirodihydrofurans.
The zwitterion formed by the reaction of dimethoxycarbene and DMAD adds efficiently to one of the carbonyl groups of 1,2-dicarbonyl compounds and anhydrides to generate dihydrofurans and spirodihydrofurans in good yields. In many cases, the carbene inserts into the C-C bond of the dione to yield masked vicinal tricarbonyl systems.
Nair
Vijay
V
Organic Chemistry Division, Regional Research Laboratory (CSIR), Trivandrum, India. vijaynair_2001@yahoo.com
Deepthi
Ani
A
Poonoth
Manojkumar
M
Santhamma
Bindu
B
Vellalath
Sreekumar
S
Babu
Beneesh Pattoorpady
BP
Mohan
Resmi
R
Suresh
Eringathodi
E
D000480:Alkynes / Q000737:chemistry*; D000812:Anhydrides / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006838:Hydrocarbons / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000480:Alkynes; D000812:Anhydrides; D005663:Furans; D006838:Hydrocarbons; D007659:Ketones; D013141:Spiro Compounds; C030011:carbene; C022918:acetylenedicarboxylic acid dimethyl ester; D008697:Methane