Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability
Catalytic enantioselective Grignard Nozaki-Hiyama methallylation from the alcohol oxidation level: chloride compensates for π-complex instability
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DOI：
10.1039/c1cc14392a
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发表时间：
2011-01-01
影响因子：
4.9
通讯作者：
Krische, Michael J.
中科院分区：
文献类型：
--
作者：
Hassan, Abbas;Townsend, Ian A.;Krische, Michael J.
甲基烯丙基氯是高对映选择性的Grignard Nozaki-Hiyama甲基化反应中有效的烯丙基供体，通过铱催化的转移氢化反应从醇或醛的氧化水平进行。在相同的条件下，乙酸甲烯丙酯不能有效地反应。经高效液相色谱分析，1，3-丙二醇的双甲基化反应提供了单一对映体的C-2对称加合物。
Methallyl chloride serves as an efficient allyl donor in highly enantioselective Grignard Nozaki-Hiyama methallylations from the alcohol or aldehyde oxidation level via iridium catalyzed transfer hydrogenation. Under identical conditions, methallyl acetate does not react efficiently. Double methallylation of 1,3-propanediol provides the C-2-symmetric adduct as a single enantiomer, as determined by HPLC analysis.