Stereoselective synthesis of polysubstituted 2,5-dihydrofurans from reaction of 1,4-dilithio-1,3-dienes with aldehydes.
[reaction: see text] Reaction of 1,4-dilithio-1,3-diene derivatives with 2 equiv of aldehydes affords polysubstituted 2,5-dihydrofurans in good to high yields with perfect regio- and stereoselectivities. Hexa-2,4-diene-1,6-dialcoholates are proposed as the first intermediates, which undergo a cyclization and subsequent elimination of Li(2)O to generate the 2,5-dihydrofuran derivatives.
Chen
Jinglong
J
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Song
Qiuling
Q
Li
Pixu
P
Guan
Hairong
H
Jin
Xianglin
X
Xi
Zhenfeng
Z
D001685:Biological Factors / Q000138:chemical synthesis; D002070:Butadienes / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism
D001685:Biological Factors; D002070:Butadienes; D005663:Furans; D009942:Organometallic Compounds; D008094:Lithium