A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND 5-SUBSTITUTED PYRROLIDINONES
A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND 5-SUBSTITUTED PYRROLIDINONES
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DOI：
10.1021/jo00032a012
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发表时间：
1992-03-13
影响因子：
3.6
通讯作者：
MEYERS, AI
中科院分区：
文献类型：
--
作者：
BURGESS, LE;MEYERS, AI
以3-酰基丙酸为起始原料，实现了高对映体纯度目标化合物的高效合成。以相应的伽马酮酸和(R)-苯甘氨酚为原料，用丙烷或三乙基硅烷与四氯化钛立体选择性还原得到手性双环内酰胺2a-h，分别得到N-取代吡咯烷和吡咯烷酮。随后对苯甘氨酚的裂解返回了所需的胺和内酰胺。用手性固定相高效液相色谱法测定这些化合物的对映体纯度为98%。
An efficient procedure for the preparation of the title compounds in high enantiomeric purity has been realized starting from 3-acylpropionic acids. Stereoselective reduction of chiral bicyclic lactams 2a-h, prepared from the corresponding gamma-keto acid and (R)-phenylglycinol, using alane or triethylsilane with titanium tetrachloride provided the N-substituted pyrrolidines and pyrrolidinones, respectively. Subsequent cleavage of the phenylglycinol returned the desired amines and lactams. The enantiomeric purity of these compounds was determined to be > 98% by chiral stationary-phase HPLC.