Asymmetric amplification using chiral cocrystals formed from achiral organic molecules by asymmetric autocatalysis

Asymmetric amplification using chiral cocrystals formed from achiral organic molecules by asymmetric autocatalysis
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DOI:
10.1002/anie.200462963
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发表时间:
2005-01-01
影响因子:
16.6
通讯作者:
Soai, K
Soai, K
中科院分区:
化学1区
文献类型:
--
作者:
Kawasaki, T;Jo, K;Soai, K

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二异丙基锌对嘧啶-5-甲醛的对映选择性加成是由色胺/对氯苯甲酸(见示意图)和3-吲哚丙酸/菲啶的非手性双组分分子晶体的手性共晶诱导的。该反应结合不对称自催化,得到高对映体过量的嘧啶基烷醇。
(Chemical Equation Presented) Enantioselective addition of diisopropyl-zinc to a pyrimidine-5-carbaldehyde was induced by chiral cocrystals of achiral two-component molecular crystals of tryptamine/para-chlorobenzoic acid (see scheme) and 3-indolepropionic acid/phenanthridine. This reaction, in conjunction with asymmetric autocatalysis, afforded a pyrimidyl alkanol in high enantiomeric excess.