76741-13-4Relevant academic research and scientific papers
The C2 selective nucleophilic substitution reactions of 2,3-epoxy alcohols mediated by trialkyl borates: The first endo-mode epoxide-opening reaction through an intramolecular metal chelate
Sasaki, Minoru,Tanino, Keiji,Hirai, Atsushi,Miyashita, Masaaki
, p. 1789 - 1791 (2007/10/03)
(Matrix presented) Highly efficient C2 selective substitution reactions of 2,3-epoxy alcohols with nucleophiles were developed by using NaN 3-(CH3O)3B, NaSPh-(CH3O) 3B, or NaCN-(C2H5/
Determination of absolute configurations of β-or γ-methyl substituted secondary alcohols by NMR spectroscopy
Takahashi, Haruko,Iwashima, Makoto,Iguchi, Kazuo
, p. 333 - 336 (2007/10/03)
A new method has been developed for determining the absolute configurations of acyclic β- or γ-methyl substituted secondary alcohols using their 2NMA esters. The 1H-NMR spectra of (R)- and (S)-2NMA esters of model compounds were measured, and Δδ values (δ(R-ester) - δ(S-ester) for the corresponding protons were compared between syn and anti compounds. Threshold values important to judging the relative stereochemistry of the two chiral centers bearing methyl and hydroxy groups were obtained. The absolute configuration of the chiral bearing a secondary hydroxy group is easily determined based on the sign of Δδ values as in the MTPA method and thus in the present study it was also possible to clearly determine the absolute configuration of the chiral center bearing a methyl group.
SYNTHESIS OF BOTH THE ENANTIOMERS OF INVICTOLIDE, A PHEROMONE COMPONENT OF THE RED IMPORTED FIRE ANT
Mori, Kenji,Nakazono, Yutaka
, p. 6459 - 6464 (2007/10/02)
Both the enantiomers of invictolide were synthesized in 17 steps from propargyl alcohol.
CHIRALITY TRANSFER IN THE ESTER ENOLATE CLAISEN REARRANGEMENT OF (R)-1-METHYL-(E)-2-BUTENYL HYDROXYACETATE AND ITS APPLICATION TO THE STEREOCONTROLLED PHEROMONE SYNTHESIS
Fujisawa, Tamotsu,Tajima, Kazuhisa,Sato, Toshio
, p. 1669 - 1672 (2007/10/02)
The ester enolate Claisen rearrangement of (R)-1-methyl-(E)-2- butenyl hydroxaacetate provides complete asymmetric transfer along with 98percent erythroselectivity to give (2R,3S)-2-hydroxy-3-methyl-(E)-4-hexenoic acid.Its synthetic utility is demonstrated by the stereocontrolled synthesis of optically active pheromones.
SYNTHESIS OF THE ENANTIOMERIC FORMS OF CIS AND TRANS 1-BENZYLOXY-2,3-EPOXY BUTANE AND OF (3S,4S) 4-METHYL-3-HEPTANOL
Fuganti, Claudio,Grasselli, Piero,Servi, Stefano,Zirotti, Carlo
, p. 4269 - 4272 (2007/10/02)
The C4 erythro and threo diols (7) and (8) are converted either into the chiral epoxides (13) and (15) or into the enantiomers (14) and (16); the epoxide (13) is used as chiral synthon for the preparation of (3S,4S) 4-methyl-3-heptanol (21).
PREPARATION OF THE BOTH ENANTIOMERS OF THREO-2-AMINO-3-METHYLHEXANOIC ACID BY ENZYMATIC. RESOLUTION AND THEIR CONVERSION TO OPTICALLY ACTIVE FORMS OF THREO-4-METHYLHEPTAN-3-OL, A PHEROMONE COMPONENT OF THE SMALLER EUROPEAN ELM BARK BEETLE
Mori, Kenji,Iwasawa, Hiroko
, p. 2209 - 2213 (2007/10/02)
The both enantiomers of threo-2-amino-3-methylhexanoic acid were prepared by resolving its racemic N-acetate with Aspergillus acylase.The amino acid enantiomers were converted to optically active forms of threo-4-methylheptan-3-ol, a pheromone component of Scolytus multistriatus.
