One-Pot Domino Aldol Reaction of Indium Enolates Affording 6-Deoxy-α-D,L-altropyranose Derivatives: Synthesis, Mechanism, and Computational Results

被引：10

作者：

Cinar, M. Emin ^{[1
]}

Schmittel, Michael ^{[1
]}

机构：

[1] Univ Siegen, Dept Biol Chem, D-57068 Siegen, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 16期

关键词：

EFFECTIVE CORE POTENTIALS; MOLECULAR CALCULATIONS; DIASTEREOSELECTIVE SYNTHESIS; CONJUGATE ADDITION; L-ALTROSE; TITANIUM; COMPLEXES; CONDENSATION; SILICON; SYN;

D O I：

10.1021/acs.joc.5b01256

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The domino-aldol-aldol-hemiacetal-reaction cascade of indium and other group 13 metal enolates furnished 6-deoxy-alpha-D,L-altropyranose derivatives in up to 99% yield under thermodynamic control. At lower temperature and thus under kinetic control, the reaction proceeded in a much less diastereoselective manner. The changeover from kinetic to thermodynamic control operating in this multistep domino-aldol-aldol-hemiacetal protocol was used for probing the efficiency of DFT computations. Calculations at the B3LYP/6-31G(d)/LANL2DZ level provided a mechanistic picture in full agreement with the experimental outcome.

引用

页码：8175 / 8182

页数：8

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