Diastereoselective hydrolysis of alpha,gamma-substituted gamma-sultones in the asymmetric synthesis of gamma-hydroxy sulfonates

作者：Enders D^*; Harnying W; Raabe G

来源：Synthesis (Germany), 2004, (4): 590-594.

DOI：10.1055/s-2004-815952

• sultones
• sulfonates
• asymmetric synthesis
• hydrolysis
• ring-opening

The hydrolysis of enantiopure alpha,gamma-substituted gamma-sultones with water under mild conditions leads to alpha,gamma-substituted gamma-hydroxy methyl sulfonates in very good yields and excellent diastereo- and enantiomeric excesses (de, ee greater than or equal to 98%). The reaction proceeds via a S(N)2 mechanism with inversion of configuration at the attacked gamma-carbon atom whose absolute configuration was established by Xray crystallography.

• 出版日期2004-3-9