一个高度enantioselective的分子内赫克反应与一个单牙联体
Rosalinde Imbos1, Adriaan J Minnaard, Ben L Feringa
1Stratingh Institute, Department of Organic Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
使用基于TADDOL的色胺酸联体的新型酶选择性内分子赫克反应有效地产生奇拉性循环色二烯. 这种方法可以达到高达96%的enantioselectivities ee,这对于Heck反应中的单联体来说是第一次.
科学领域:
- 有机化学 有机化学
- 不对称的催化剂.
背景情况:
- 分子内赫克反应是形成C-C键的强大工具.
- 开发高效的enantioselective变体仍然是一个重大挑战,特别是单联体.
研究的目的:
- 为了开发一个有效的enantioselective分子内赫克反应为cyclohexadienones.
- 为了利用随时可用的TADDOL基胺酸联体.
- 在没有额外的添加剂的情况下实现高的enantioselectivity.
主要方法:
- 内部分子赫克反应使用循环二烯作为基质.
- 使用基于TADDOL的模块化单酸和双酸胺酸作为合性连接剂.
- 优化反应条件以避免添加剂.
主要成果:
- 成功开发了一种高效的酶选择性分子内赫克反应.
- 取得了优异的反选择性,达到高达96%的EE.
- 在赫克反应中首次证明了单酸胺酸联体在实现高反选择性方面的有效性.
结论:
- 开发的方法提供了一条新且高效的途径,以获得基丰富的环二烯.
- 基于TADDOL的光胺基是对不对称的Heck反应的有效合联结体.
- 没有添加剂简化了反应协议,并扩大了它的适用性.
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