356049-96-2

Upstream product

• 3144-09-0 methanesulfonamide 
• 132960-14-6 Weinreb amide of 2-methyl-2-propeonic acid 

Downstream Products

• 241148-19-6 (R)-2,3-Dihydroxy-2-methyl-propionic acid benzyl ester 

Relevant academic research and scientific papers

New syntheses of enantiopure 2-methyl isoserines

Herein we describe the synthesis of the two enantiomerically pure 3-amino-2-hydroxy-2-methylpropionic acids - (S)- and (R)-α-methyl isoserines - starting from the chiral diols (S)- and (R)-2,3-dihydroxy-N- methoxy-2,N-dimethylpropionamides, respectively, which were obtained by Sharpless asymmetric dihydroxylation (AD) of the olefin N-methoxy-2,N- dimethylacrylamide with AD-mix α or β as chiral catalytic ligands.

An efficient synthesis of the 1,6-dioxaspiro[4.4]nonan-2-one motif of the immunosuppressive triterpenoid Phainanoid F

We describe an efficient synthesis of the 1,6-dioxaspiro[4.4]nonan-2-one motif of the immunosuppressive triterpenoid Phainanoid F and its C4 epimer. A furan oxidative spirocyclization for constructing the spiro center was used as the key step. Other important reactions involved Sharpless asymmetric dihydroxylation, Weinreb ketone synthesis and Yamaguchi esterfication. The synthesis was achieved in 11 linear steps with 17.3% overall yield.

Enantioselective Total Syntheses of (R)- A nd (S)-Naphthotectone, and Stereochemical Assignment of the Natural Product

Both isomers of naphthotectone, an isoprenoid quinone from Verbenaceae Tectona grandis possessing interesting biological activities, were enantioselectively obtained by two different synthetic routes in which the carbon side-chain of the naphthoquinone core was introduced using either a Sonogashira or a Heck coupling reaction. In both cases, the naphthoquinone core of the final products was obtained by a late-stage anodic treatment. (R)-Naphthotectone was obtained in six steps from leuconaphthazarin with an overall yield of 38 % and an enantiomeric excess of 86 %. This compound was found to have the same absolute configuration as the natural product at its C-3′ stereogenic center. (S)-Naphthotectone was obtained in five steps from leuconaphthazarin with an overall yield of 36 % and an enantiomeric excess of 80 %. Naphthotectone was synthesized in both racemic and enantioenriched forms by two different synthetic strategies using Pd coupling reactions and anodic treatment as key steps. The stereochemistry of the natural product has been assigned.

SN2 vs. E2 on quaternary centres: An application to the synthesis of enantiopure β2,2-amino acids

SN2 and E2 competing reactions in cyclic sulfamidates can be modulated by the change of an amide group to an ester group attached to the quaternary carbon activated for the nucleophilic attack, allowing an easy approach to enantiopure α,α-disub

Enantioselective synthesis of α-methyl-D-cysteine and lanthionine building blocks via α-methyl-d-serine-β-lactone

(Matrix presented) We report here the enantioselective synthesis of Boc-α-methyl-D-cysteine(PMB)-OH and lanthionine building blocks through the regioselective ring opening of key intermediate Boc-α -methyl-D-serine-β-lactone.

Enantioselective synthesis of (S)- and (R)-α-methylserines: Application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals

This report describes the synthesis of enantiomerically pure (S)- and (R)-α-methylserines on a multigram scale, starting from the Weinreb amide of 2-methyl-2-propenoic acid and using a stereodivergent synthetic route that involves a Sharpless asymmetric dihydroxylation reaction. As a synthetic application of these quaternary α-amino acids, they were used as starting materials in the synthesis of the well-known valuable homochiral (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinal building blocks.

Asymmetric dihydroxylation (AD) of N,N-dialkyl and N-methoxy-N-methyl α,β- and β,γ-unsaturated amides

The asymmetric dihydroxylation of α,β- and β,γ-unsaturated amides affords the corresponding diols in good yields and excellent enantiomeric excesses. However, both N,N-dialkyl and N-methoxy-N-methyl α,β- and β,γ-unsaturated amides require a Modified-AD-mix formulation to achieve good catalytic turnover rates.