(S)和(R)-3-甲基辛酸甲酯的合成新方法

A new synthesis method for (S) and (R) methyl 3-methyl-octanoate

以天然樟脑衍生物莰烷 -1 0 ,2 -磺内酰胺为原料 ,在有或无 Cu I催化条件下 ,以巴豆酰基莰烷 -1 0 ,2 -磺内酰胺的不对称 Michael加成反应为关键步骤 ,进行了合成。其加成产物 ( 3′S)和 ( 3′R) -N-3′-甲基辛酰基莰烷 -1 0 ,2 -磺内酰胺经 Li OH-H2 O2 水解及甲醇酯化反应即可合成目标产物 ( S)和 ( R) -3-甲基辛酸甲酯。全合成总产率 5 3% ,目标产物对映异构体纯度可达 96%

S) and (R) methyl 3 methyloctanoate were synthesized from R camphor derivative bornane 10,2 sultam via asymmetric Michael addition of N crotonoylbornane 10,2 sultam in the presence and absence of CuI as key step. The addition products (3′ S ) and (3′ R ) N 3′ methyloctanoyl bornane 10,2 sultam were hydrolyzed with LiOH H 2O 2,and esterified with methanol to give the target products.The yield of the total synthesis is over 53% and the enantiomeric excess of the products is over 96% ee.