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• W2054863460 abstract "Abstract Experimental and theoretical investigations of the anti-selective nucleophilic addition induced by BF 3 to 3-formyl-Δ 2 -isoxazolines are described. Ab initio molecular orbital (MO) calculations show that the 3-formyl-Δ 2 -isoxazoline-BF 3 complex prefers s-trans conformation to s-cis conformation. Nucleophiles attack the stable s-trans conformer from the opposite side of C(4) substituent, giving anti-adducts selectively. The BO bond lengths and the stabilization energies suggest that the features of the complex resemble those of aliphatic aldehyde-BF 3 complexes. Introduction of substituent to allyl tin improves the anti-selectivity from 87/13 to 98/2. These results suggest that the reaction proceeds via anti-periplanar transition state." @default.
• W2054863460 created "2016-06-24" @default.
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• W2054863460 date "1993-08-01" @default.
• W2054863460 modified "2023-09-25" @default.
• W2054863460 title "An experimental and theoretical study on stereoselective addition to 3-formyl-Δ2-isoxazolines. Part 1. 1,3-anti-selectivity induced by BF3·OEt2" @default.
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• W2054863460 doi "https://doi.org/10.1016/s0040-4020(01)87239-2" @default.
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