95201-27-7Relevant academic research and scientific papers
Asymmetric synthesis of dihydroindanes by convergent alkoxide-directed metallacycle-mediated bond formation
Greszler, Stephen N.,Reichard, Holly A.,Micalizio, Glenn C.
, p. 2766 - 2774 (2012/03/22)
A convergent synthesis of highly substituted and stereodefined dihydroindanes is described from alkoxide-directed Ti-mediated cross-coupling of internal alkynes with substituted 4-hydroxy-1,6-enynes (substrates that derive from 2-directional functionaliza
Room-temperature metallation of 2-substituted 1,3-dithiane derivatives and subsequent coupling with 2,3-disubstituted oxiranes
Ide, Mitsuaki,Nakata, Masaya
, p. 2491 - 2499 (2007/10/03)
2-Substituted 1,3-dithiane derivatives, (S)-1(t-butyldiphenylsiloxy)-2- (1,3-dithian-2-yl)propane (9), (S)-1-(t-butyldimethylsiloxy)-2-(1,3-dithian- 2-yl)propane, 1-(t-butyldiphenylsiloxy)-2-(1,3-dithian-2-yl)-2-methylpropane, and 1,2-bis-(t-butyldiphenylsiloxy)-3-(1,3-dithian-2-yl)propane, were subjected to lithiation in THF with n-BuLi at room temperature (r.t.); the resulting anions reacted with 2,3-disubstituted oxirane, trans-2-methyl-3- (triphenylmethoxymethyl)oxirane(22), at r.t., giving the coupling products in satisfactory yield. On the other hand, the lithium salt formed in ether from (S)2-(1,3-dithian-2-yl)-1-(4-methoxybenzyloxy)propane with n-BuLi at r.t. reacted with 22 at r.t. in the presence of hexamethylphosphoric triamide to afford the coupling product in moderate yield. In addition, a mixed organometallic reagent, n-BuLi/Bu2Mg, was found to be an effective metallation reagent for 9 and the resulting anion reacted with 22 to afford the coupling product in good yield.
The preparation of L-(2S,3S)-4,4,4-[2H3] valine
Shattuck, James C.,Meinwald, Jerrold
, p. 8461 - 8464 (2007/10/03)
Isotopically labeled amino acids are important for protein structure determination and in biosynthetic studies. We report now on the synthesis of(2S,3S)-4,4,4-[2H3] valine (9) using a short, versatile, enzyme-free procedure. The deut
First Example of Reversal of Normal Stereoselectivity in the Intramolecular Pauson-Khand Reaction
Casalnuovo, Joseph A.,Scott, Robert W.,Harwood, Eric A.,Schore, Neil E.
, p. 1153 - 1156 (2007/10/02)
Stereoselectivity favoring exo substituent orientation in the intramolecular Pauson-Khand reaction of 3-methyl-4-hydroxy-1,6-heptenynes to form bicyclooctenones is affected by the relative stereochemistry at C3 and C4.Cycloaddition of one stereoiso
Stereoselective Synthesis of the C-8 to C-15 Moiety of Erythronolide A
Hoagland, Steven,Morita, Yasushi,Bai, Dong Lu,Maerki, Hans-Peter,Kees, Kenneth,et al.
, p. 4730 - 4735 (2007/10/02)
Enantiomerically pure ketone 2, corresponding to the C-8, C-15 segment of erythronolide A, has been prepared by a 12-step route with crotyl alcohol as starting material in 5-6percentoveral yield.The synthesis starts with trisylhydrazone 4, which is conver
DIASTEREO- AND ENANTIOSELECTIVE PREPARATION OF β-ALKYLHOMOALLYLIC ALCOHOLS SYNTHESIS OF SERRICORNIN AND CORYNOMYCOLIC ACID
Kobayashi, Yuichi,Kitano, Yasunori,Takeda, Yoshiyuki,Sato, Fumie
, p. 2937 - 2944 (2007/10/02)
A new and efficient method for the preparation of four possible stereoisomers of β-alkylhomoallylic alcohols 1 has been developed which is based on the diastereoselective addition of nucleophiles to optically active α-alkyl-β-trimethylsilyl-β,γ-unsaturate
