2,3-PYRROLIDINEDICARBOXYLATES AS NEUROTRANSMITTER CONFORMER MIMICS - ENANTIOSELECTIVE SYNTHESIS VIA CHELATION-CONTROLLED ENOLATE ALKYLATION
2,3-PYRROLIDINEDICARBOXYLATES AS NEUROTRANSMITTER CONFORMER MIMICS - ENANTIOSELECTIVE SYNTHESIS VIA CHELATION-CONTROLLED ENOLATE ALKYLATION
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DOI：
10.1021/jo00088a030
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发表时间：
1994-05-06
影响因子：
3.6
通讯作者：
CHAMBERLIN, AR
中科院分区：
文献类型：
--
作者：
HUMPHREY, JM;BRIDGES, RJ;CHAMBERLIN, AR
Conformationally restricted analogs of naturally-occurring amino acids can serve in a variety of ways as protein structure/function probes. A diastereo- and enantioselective synthesis of the four stereoisomers of 2,3-pyrrolidinedicarboxylic acid (an analog of aspartic acid) are described in this paper. The key step is a Rapoport-type aspartate alkylation that can be controlled to give good yields of either diastereomer as a function of enolate geometry. A novel type of chelation control is proposed to account for these results.
