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- W2772067484 abstract "Abstract Recently, we found that the Diels–Alder reaction between levoglucosenone and the acetonide of (1 S ,2 R )‐3‐methylcyclohexa‐3,5‐diene‐1,2‐diol occurs through the most hindered face of the diene. This unexpected facial selectivity has no precedent for di‐ O ‐isopropylidene‐protected dienes, and the reasons behind it remain unclear. Here, we expand on our earlier findings, computationally assessing the structural and electronic factors responsible for this unforeseen stereoselectivity. The B3LYP/6‐31+G(d,p) results identify the three main adducts (β‐ endo ‐ ortho :α‐ endo ‐ meta :α‐ exo ‐ ortho ), giving a product ratio (63:9:28) that is in line with the experimental value (64:16:10). The β‐ endo attack allows to maximize the electrostatic attraction between the reactants, giving rise to dipolar C−O⋅⋅⋅H−C interactions with the isopropylidene group at the transition state. The endo / exo preference can be rationalized through electrostatic repulsion and steric hindrance between the isopropylidene and methylene fragments. Finally, the non‐classical C=O⋅⋅⋅H−C hydrogen bonding stabilizes the ortho transition structures, making them more polar and asynchronous." @default.
- W2772067484 created "2017-12-22" @default.
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- W2772067484 date "2017-12-01" @default.
- W2772067484 modified "2023-09-27" @default.
- W2772067484 title "Diels-Alder Reaction of Levoglucosenone with a Protected cis -Cyclohexadienediol: Structural and Electronic Basis behind the Unexpected Stereoselectivity" @default.
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- W2772067484 doi "https://doi.org/10.1002/slct.201702442" @default.
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