Asymmetric synthesis of (R)- and (S)-2-pyrrolidinemethanesulfonic acid

Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs

“…The same methodology was applied for the asymmetric synthesis of (R)-and (S)-2-pyrrolidinemethanesulfonic acid starting from a cyclic alcohol as (R)-and (S)-2-pyrrolidinemethanol 137 (R 1 R ¼ -(CH 2 ) 3 -, Scheme 13.27) affording the corresponding compounds with an enantiomeric purity >99%. 77 However, when starting from chiral b-amino secondary alcohols 141, the asymmetric synthesis of the b-aminoalkanesulfonic acids 140 was carried out following the same methodology, but in this case an inversion of configuration was observed 78 (Scheme 13.28, Table 13.3). Along with these observations, Xu 79 has proposed a mechanism based on a neighboring-group-assisted cyclization to a 2-alkylaziridine 142 formed from both primary b-amino alcohol 137 or secondary bamino alcohol 141 (Scheme 13.28).…”

An Expeditious Synthesis of 1-Substituted and Cyclic Taurines

“…5 There are three types of structural analogues of naturally occurring amino acids of b-aminoalkanesulfonic acids, which include 1-substituted taurines, 2-substituted taurines, and 1,2-disubstituted taurines (Figure 1). 2-Substituted taurines have been synthesized effectively via sulfite displacement of the methanesulfonates of the vicinal amino alcohols, [8][9][10][11][12][13] the peroxy acid oxidation of the thioacetates of vicinal amino primary alcohols, [14][15][16][17][18][19] aminosulfonation of alkenes, 20 and sulfite ring-opening of aziridines. 21 However, there has been little attention paid to the synthesis of 1-substituted taurines.…”

A General Route to the Synthesis of N-Protected 1-Substituted and 1,2-Disubstituted Taurines

“…8 There are three types of structural analogues of naturally occurring amino acids for b-aminoalkanesulfonic acids, which include 1-substituted taurines, 2-substituted taurines, and 1,2-disubstituted taurines (Figure 1). 2-Substituted taurines have been synthesized effectively from b-amino primary alcohols, [9][10][11][12][13][14][15][16][17][18] which were easily obtained by reduction of natural amino acids, from b-amino secondary alcohols 19,20 via sulfite displacement of their methanesulfonates, [9][10][11][12] peroxy acid oxidation of their thioacetates, [13][14][15][16][17]21 and sulfite ringopening of aziridines. 18 But little attention has been paid to the synthesis of 1-substituted and 1,2-disubstituted taurines 15,21,22 and their sulfonopeptides.…”