356048-04-9Relevant articles and documents
A synthesis of optically active α-quaternary α-amino acids and esters by assembling three components, ketones, (R)-chloromethyl p-tolyl sulfoxide, and sodium azide, via sulfinyloxiranes
Satoh, Tsuyoshi,Hirano, Mizue,Kuroiwa, Akio,Kaneko, Youhei
, p. 9268 - 9279 (2007/10/03)
Treatment of lithium α-sulfinyl carbanion of chloromethyl p-tolyl sulfoxides with ketones at low temperature afforded adducts in almost quantitative yields, which were exposed to t-BuOK to give sulfinyloxiranes in high yields. The sulfinyloxirane was reac
Enantioselective synthesis of α-methyl-D-cysteine and lanthionine building blocks via α-methyl-d-serine-β-lactone
Smith, Nicole D.,Goodman, Murray
, p. 1035 - 1037 (2007/10/03)
(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.
Understanding the unusual regioselectivity in the nucleophilic ring-opening reactions of gem-disubstituted cyclic sulfates. Experimental and theoretical studies
Avenoza, Alberto,Busto, Jesus H.,Corzana, Francisco,Garcia, Jose I.,Peregrina, Jesus M.
, p. 4506 - 4513 (2007/10/03)
The regioselectivity of the nucleophilic ring-opening reactions of three gem-disubstituted cyclic sulfates with sodium azide has been studied from both experimental and theoretical viewpoints. It is found that, depending on the substituent present in the cyclic sulfate, the reaction displays reversed regioselectivity, which allows one or another regioisomer to be obtained with selectivities greater than 4:1. The theoretical calculations show that, contrary to previous understanding, the intrinsic preference in all cases is azide attack at the less-substituted Cβ position, a consequence of similar stereoelectronic effects in the three sulfates considered. The observed preference for Cα attack in the case of the ester sulfate is explained in terms of differential solvent effects, which are in turn due to subtle differences in the charge transfer in the different transition structures.
Enantioselective synthesis of (S)- and (R)-α-methylserines: Application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals
Avenoza, Alberto,Cativiela, Carlos,Corzana, Francisco,Peregrina, Jesus M.,Sucunza, David,Zurbano, Maria M.
, p. 949 - 957 (2007/10/03)
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.
