lithium (S)-N-allyl-N-α-methylbenzyl amide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: lithium (S)-N-allyl-N-α-methylbenzyl amide
• 英文别名: lithium (S)-N-allyl-N-α-methylbenzylamide；lithium allyl-(S)-1-phenylethylamide；(S)-lithium N-allyl-N-α-methylbenzylamide；lithium;[(1S)-1-phenylethyl]-prop-2-enylazanide
• 化学式: C₁₁H₁₄N*Li
• 分子量: 167.18
• InChiKey: LHWKPKNCLRISHR-PPHPATTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.31
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  lithium (S)-N-allyl-N-α-methylbenzyl amide 在 二异丁基氢化铝 、 sodium amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (4S,αS)-4-N-allyl-N-α-methylbenzylamino-hept-1-ene
  参考文献：
  名称：

  Ring Closing Metathesis for the Asymmetric Synthesis of (S)-Homopipecolic Acid, (S)-Homoproline and (S)-Coniine

  摘要：

  通过(S)-N-烯丙基-N-α-甲基苄胺锂的对映选择性共轭加成到α,β-不饱和酯或Weinreb酰胺上，然后进行环合复分解反应，可以高度对映选择性地获得环状β-氨基酸(S)-高哌考酸和(S)-高脯氨酸以及胺(S)-毒芹碱。

  DOI：

  10.1055/s-2002-32580

文献信息

• The use of lithium (α-methylbenzyl)allylamide for the asymmetric synthesis of unsaturated β-amino acid derivatives
  作者：Stephen G. Davies、David R. Fenwick、Osamu Ichihara

  DOI：10.1016/s0957-4166(97)00470-9

  日期：1997.10

  The unsaturated β-amino acid derivatives (3R)-(E)-3-(N-tert-butoxy-carbonyl)aminohex-4-enoate and methyl (2S,3S)-3-(N-tert-butoxycarbonyl)-amino-2-hydroxyhex-4-enoate have been synthesised from lithium (S)-(α-methylbenzyl)allylamide and (E,E)-tert-butyl hex-2,4-dienoate. After a highly stereoselective conjugate addition of the lithium amide to the α,β-unsaturated ester, or a highly stereoselective

  不饱和β氨基酸衍生物（3 - [R ）- （ê）-3-（ñ -叔丁氧基羰基）氨基己-4-烯酸乙酯和甲基（2-小号，3小号）-3-（ñ -叔丁氧羰基（S）-（α-甲基苄基）烯丙基酰胺锂和（E，E）-叔丁基合成了）-氨基-2-羟基己基-4-烯酸酯-2,4-己二酸正丁酯。在将酰胺锂高度立体选择的共轭加成到α，β-不饱和酯上或高度立体选择性的共轭加成-亲电羟基化之后，加合物被脱甲酸酯化，并且所得仲胺转化为苯甲酰胺或恶唑烷酮。的Ñ - α -甲基苄基基团，然后用甲酸或使用溶解金属还原除去。这些脱保护程序使分子中的不饱和度保持完整。
• Asymmetric synthesis of homochiral Baylis–Hillman products employing (R)-N-methyl-N-α-methylbenzyl amide
  作者：Stephen G Davies、Christian A.P Smethurst、Andrew D Smith、G.Darren Smyth

  DOI：10.1016/s0957-4166(00)00224-x

  日期：2000.6

  The conjugate addition of (R)-N-methyl-N-alpha-methylbenzyl amide to tert-butyl cinnamate followed by an asymmetric aldol reaction and subsequent N-oxidation/Cope elimination affords beta-substituted homochiral Baylis-Hillman products in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Synthesis of Enantiomerically Pure 2,2,3,4,5-Pentasubstituted Pyrrolidines by Phenylsulfanyl Migration
  作者：I. Craig Baldwin、Paul Briner、Martin D. Eastgate、David J. Fox、Stuart Warren

  DOI：10.1021/ol0268384

  日期：2002.12.1

  [GRAPHICS]Enantiomerically pure 2,2,3,4,5-pentasubstituted pyrrolidines can be prepared, in high overall yield, from alpha-,beta-unsaturated esters. Asymmetry is introduced via a Michael addition, and additional stereogenic centers are introduced by an aldol reaction. A novel stereospecific ring-forming reaction, proceeding via a thiiranlum (episulfonium) ion, yields pyrrolidines from beta-hydroxy sulfides. In this manner, 2,2,3,4,5-pentasubstituted pyrrolidines, containing three contiguous stereogenic centers around the ring, can be prepared in 44% overall yield from ethyl crotonate.
• Asymmetric synthesis of a homochiral differentially protected pseudo-meso bis-β-amino acid scaffold
  作者：Steven D. Bull、Stephen G. Davies、Andrew D. Smith

  DOI：10.1016/s0957-4166(01)00544-4

  日期：2001.11

  A strategy for the asymmetric synthesis of a homochiral differentially protected pseudo-meso bis-beta-amino acid scaffold utilising the conjugate addition of homochiral lithium amides and subsequent selective deprotection is demonstrated. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A stereocontrolled approach to 1β-methylcarbapenem
  作者：Stephen G. Davies、Charles J.R. Hedgecock、Jeffrey M. McKenna

  DOI：10.1016/0957-4166(95)00079-5

  日期：1995.4

  Conjugate addition of lithium N-allyl-N-alpha-methylbenzylamide to chiral alpha,beta-unsaturated esters is subject to double stereodifferentiation, the mismatched pair reaction allowing access to an intermediate for 1 beta-methylcarbapenem synthesis.