120409-97-4Relevant articles and documents
Kinetic resolution of 2-furylcarbinols using the Sharpless oxidation and its application to the synthesis of (5R,6S)-6-acetoxy-5-hexadecanolide
Kametani, Tetsuji,Tsubuki, Masayoshi,Tatsuzaki, Yoko,Honda, Toshio
, p. 2107 - 2110 (1988)
Kinetic resolution of 2-furylcarbinols employing 10 mol% of Ti(OiPr)4 in the presence of molecular sieves 3A under the Sharpless oxidation condition generally affords corresponding optically active 2-furylcarbinols in a range of 80-9
Copper-dipyridylphosphine-catalyzed hydrosilylation: Enantioselective synthesis of aryl- and heteroaryl cycloalkyl alcohols
Qi, Shan-Bin,Li, Min,Li, Shijun,Zhou, Ji-Ning,Wu, Jun-Wen,Yu, Feng,Zhang, Xi-Chang,Chan, Albert S.C.,Wu, Jing
, p. 929 - 937 (2013/02/26)
The non-precious metal copper-catalyzed enantioselective hydrosilylation of a vast array of aryl cycloalkyl ketones with different ring sizes was studied systematically for the first time (up to 99% enantiomeric excess). The results demonstrated that the
Room temperature and highly enantioselective additions of alkyltitanium reagents to aldehydes catalyzed by a titanium catalyst of (R)-h 8-binol
Li, Qinghan,Gau, Han-Mou
experimental part, p. 929 - 939 (2012/06/29)
Three alkyltitanium reagents of RTi(O-i-Pr)3 (R = Cy (1a), i-Bu (1b), and n-Bu (1c)) were prepared in good yields. The high-resolution mass spectroscopy showed that 1b and 1c in the gas phase are monomeric species. However, the solid state of 1a revealed a dimeric structure. Asymmetric additions of 1a-1c to aldehydes catalyzed by a titanium catalyst of (R)-H 8-BINOL were studied at room temperature. The reactions produced desired secondary alcohols in good yields with good to excellent enantioselectivities of up to 94% ee. Reactivity and enantioselectivity differences, in terms of steric bulkiness of the R nucleophiles, are herein described. The addition reactions of secondary c-hexyl to aldehydes were slower than the reactions of primary i-butyl or n-butyl nucleophiles. For the primary alkyls, lower enantioselectivities were obtained for products from addition reactions of the linear n-butyl as compared with the enantioselectivities of products from the addition reactions of the branched i-butyl group. The same stereochemistry of RTi(O-i-Pr)3 addition reactions as the addition reactions of organozinc, organoaluminum, Grignard, or organolithium reagents directly supports the argument of that titanium-catalyzed addition reactions of aldehydes involve an addition of an organotitanium nucleophile.
Catalytic enantioselective synthesis of sterically demanding alcohols using di(2°-alkyl)zinc prepared by the refined Charette's method
Hatano, Manabu,Mizuno, Tomokazu,Ishihara, Kazuaki
supporting information; experimental part, p. 5443 - 5445 (2010/10/04)
A highly practical, catalytic enantioselective 2°-alkyl addition to aldehydes and ketones was developed. Chiral phosphoramide ligand (1) with salt-free and solvent-free di(2°-alkyl)zinc reagents prepared from (2°-alkyl)MgCl was essential. The Royal Society of Chemistry 2010.
Synthesis of Optically Active 2-Furylmethanols as Useful Chiral Building Blocks and Its Application to the Synthesis of (5R,6S)-6-Acetoxyhexadecan-5-olide and (+)-Disparlure
Kametani, Tetsuji,Tsubuki, Masayoshi,Tatsuzaki, Yoko,Honda, Toshio
, p. 639 - 646 (2007/10/02)
Kinetic resolution of racemic secondary 2-furylmethanols using catalytic amounts of the titanium(IV)-tartrate complex was achieved successfully, providing optically active 2-furylmethanols (80 - >98percent ee) and corresponding pyranones. (S)-1-(2-Furyl)undecanol (1f) was utilised as a chiral building block in the synthesis of (5R,6S)-6-acetoxyhexadecan-5-olide and (+)-disparlure.
