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January 1, 1993Journal of the Chemical Society Chemical Communications

Studies in the asymmetric ring opening of an oxabicyclic compound. Catalytic asymmetric induction using (–)-sparteine

Mark Lautens Christopher Gajda Pauline Chiu

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Abstract

Oxabicyclo[3.2.1]octenes have been found to undergo enantioselective ring opening in the presence of a catalytic quantity of the chiral amine sparteine.

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Lautens et al. (1993) studied this question.

synapsesocial.com/papers/6a94c7ea0cd128b82100a9d4 https://doi.org/10.1039/c39930001193

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Synapse has enriched 5 closely related papers on similar clinical questions. Consider them for comparative context:

1Ring Opening Reactions of Oxabicyclic Compounds as a Route to Cyclic and Acyclic Compounds with Multiple StereocentersOriginal Research · 1993 · 98 citations
2Opening of oxabicyclo[3.2.1]octenes with organolithium reagents. A route to cyclic and acyclic compounds with high stereocontrolOriginal Research · 1990 · 41 citations
3Reductive Ring‐Opening of Oxabicyclic Compounds with Diisobutylaluminum Hydride. Application to the Synthesis of the C<sub>17</sub>–C<sub>23</sub> Subunit of IonomycinOriginal Research · 1993 · 38 citations
4Optical resolution of 7‐oxabicyclo[2.2.1]hept‐21‐ene derivatives. Diastereoselectivity in the formation of cyanohydrine‐brucine complexesOriginal Research · 1984 · 80 citations
5Total synthesis of (+)-(1,2,3/4,5)-2,3,4,5-tetrahydroxycyclohexane-1-methanol and (+)-(1,3/2,4,5)-5-amino-2,3,4-trihydroxycyclohexane-1-methanol [(+)-validamine]. X-Ray crystal structure of (3S)-(+)-2-exo-bromo-4,8-dioxatricyclo[4.2.1.O]nonan-5-oneOriginal Research · 1985 · 67 citations

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