75689-30-4Relevant academic research and scientific papers
Regio- and Diastereoselective Organo-Zinc-Promoted Arylation of trans-2,3-Diaryloxiranes by Arylboronic Acids: Stereoselective Access to trans-2,3-Diphenyl-2,3-dihydrobenzofuran
Laurita, Teresa,Chiummiento, Lucia,Funicello, Maria,D'Orsi, Rosarita,Sallemi, Deborah,Tofani, Daniela,Lupattelli, Paolo
, p. 4397 - 4403 (2019/07/15)
ortho-Oxo substituted trans 2,3-diaryloxiranes were regio- and stereoselectively arylated by arylzinc reagents, obtained from the corresponding boronic acids by B–Zn exchange. The reaction was quite general, irrespective to the aryl nucleophile and proceeded via a ring opening at the α-carbon with respect to the substituted aryl ring. The stereoselectivity was from high to complete toward the alcohol resulted from retention of configuration at the electrophilic carbon. The method allowed a direct and high yielding access to trans 2,3-diphenyl-2,3-dihydrobenzofuran, which is a key structural motif in resveratrol dimers as viniferins. The use of enantioenriched starting diaryloxiranes resulted in no loss of stereochemical integrity in the final trans 2,3-dihydrobenzofuran, which was characterized for the first time in enantioenriched form.
A regioselective lithiation of ortho-cresols using the bis(dimethylamino)phosphoryl group as a directing group: General synthesis of 2,3-dihydrobenzo[b]furans including naturally occurring neolignans
Watanabe,Kawanishi,Akiyoshi,Furukawa
, p. 3123 - 3131 (2007/10/02)
A general synthetic method was developed for 2-aryl-2,3-dihydrobenzo[b]furans via regioselective lithiation of ortho-tolyl tetramethylphosphorodiamidates followed by addition of aromatic aldehydes as a key step. ortho-Tolyl tetramethylphosphorodiamidates
BASE INDUCED REACTION OF SILACYCLOBUTANE WITH ALDEHYDE OR EPOXIDE
Takeyama, Yoshihiro,Oshima, Koichiro,Utimoto, Kiitiro
, p. 6059 - 6062 (2007/10/02)
The reaction of silacyclobutane with benzaldehyde in the presence of a catalytic amount of potassium t-butoxide gave six-membered cyclic silyl ether.Meanwhile, treatment of a mixture of silacyclobutane and epoxide with lithium diisopropylamide provided si
Formation of Alcohols from Alkenes with TiCl4-NaBH4
Kano, Shinzo,Tanaka, Yasuyuki,Hibino, Satoshi
, p. 414 - 415 (2007/10/02)
The reaction of alkenes with TiCl4-NaBH4 in 1,2-dimethoxyethane afforded alcohols, the hydroxy group of which was introduced in an anti-Markovnikov direction.
