Asymmetric conjugate reductions with samarium diiodide:: asymmetric synthesis of (2S,3R)- and (2S,3S)[2-2H,3-2H]-leucine-(S)-phenylalanine dipeptides and (2S,3R)[2-2H,3-2H]-phenylalanine methyl ester
Asymmetric conjugate reductions with samarium diiodide:: asymmetric synthesis of (2S,3R)- and (2S,3S)[2-2H,3-2H]-leucine-(S)-phenylalanine dipeptides and (2S,3R)[2-2H,3-2H]-phenylalanine methyl ester
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DOI：
10.1039/b500566c
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发表时间：
2005-01-01
影响因子：
3.2
通讯作者：
Smith, AD
中科院分区：
文献类型：
--
作者：
Davies, SG;Rodríguez-Sola, H;Smith, AD
研究了二碘化钐和D_2O促进的纯手性（E）-和（Z）-亚苄基和亚异丁基二酮哌嗪（E）-5，7和（Z）-6，8的共轭还原反应。该方法允许不对称合成甲基（2S，3R）-二氘代苯丙氨酸27（de>= 95%且ee>98%）和（2S，3R）-或（2S，3S）-二氘代亮氨酸-（S）-苯丙氨酸二肽37和38（de分别为66%和74%）。提出了一种机制来解释这一过程。
The highly diastereoselective samarium diiodide and D2O-promoted conjugate reduction of homochiral (E)- and (Z)-benzylidene and isobutylidene diketopiperazines (E)-5,7 and (Z)-6,8 has been demonstrated. This methodology allows the asymmetric synthesis of methyl (2S,3R)-dideuteriophenylalanine 27 in >= 95% de and >98% ee, and (2S,3R)- or (2S,3S)-dideuterioleucine-(S)-phenylalanine dipeptides 37 and 38 in moderate de, 66% and 74% respectively. A mechanism is proposed to account for this process.