Catalysis of the Hajos-Parrish-Eder-Sauer-Wiechert reaction by cis- and trans-4,5-methanoprolines:: Sensitivity of proline catalysis to pyrrolidine ring conformation
被引:60
作者:
Cheong, PHY
论文数: 0引用数: 0
h-index: 0
机构:Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Cheong, PHY
Houk, KN
论文数: 0引用数: 0
h-index: 0
机构:
Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USAUniv Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Houk, KN
[1
]
Warrier, JS
论文数: 0引用数: 0
h-index: 0
机构:Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Warrier, JS
Hanessian, S
论文数: 0引用数: 0
h-index: 0
机构:Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Hanessian, S
机构:
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
Methanoprolines are found to be catalysts for the Hajos-Parrish-Eder-Sauer-Wiechert reaction.([1]) cis-4,5-Methanoproline exhibits catalytic ability similar to proline (86% yield, 93% ee), whereas the trans-4,5-methanoproline is less selective (67% yield, 83% ee) and shows less acceleration. The reaction was also studied with hybrid density functional theory (B3LYP). The nearly planar cis-4,5-methanoproline amine better reflects the planar iminium of the transition states than the pyramidalized trans-4,5-methanoproline. This difference in conformation is responsible for the observed higher enantioselectivity and enhanced catalytic behavior of the cis-4,5-methanoproline.
机构:
Sci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
Hayashi, Y
论文数: 引用数:
h-index:
机构:
Yamaguchi, J
Sumiya, T
论文数: 0引用数: 0
h-index: 0
机构:
Sci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
Sumiya, T
Shoji, M
论文数: 0引用数: 0
h-index: 0
机构:
Sci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
机构:
Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Hayashi, Y
Tsuboi, W
论文数: 0引用数: 0
h-index: 0
机构:Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Tsuboi, W
Ashimine, I
论文数: 0引用数: 0
h-index: 0
机构:Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Ashimine, I
Urushima, T
论文数: 0引用数: 0
h-index: 0
机构:Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Urushima, T
Shoji, M
论文数: 0引用数: 0
h-index: 0
机构:Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Shoji, M
Sakai, K
论文数: 0引用数: 0
h-index: 0
机构:Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
机构:
Sci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
Hayashi, Y
论文数: 引用数:
h-index:
机构:
Yamaguchi, J
Sumiya, T
论文数: 0引用数: 0
h-index: 0
机构:
Sci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
Sumiya, T
Shoji, M
论文数: 0引用数: 0
h-index: 0
机构:
Sci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan
机构:
Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, JapanSci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Hayashi, Y
Tsuboi, W
论文数: 0引用数: 0
h-index: 0
机构:Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Tsuboi, W
Ashimine, I
论文数: 0引用数: 0
h-index: 0
机构:Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Ashimine, I
Urushima, T
论文数: 0引用数: 0
h-index: 0
机构:Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Urushima, T
Shoji, M
论文数: 0引用数: 0
h-index: 0
机构:Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan
Shoji, M
Sakai, K
论文数: 0引用数: 0
h-index: 0
机构:Sci Univ Tokyo, Dept Ind Chem, Fac Engn, Shinjuku Ku, Tokyo 1628601, Japan