Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons

Holmstedt, Suvi; George, Lijo; Koivuporras, Alisa; Valkonen, Arto; Candeias, Nuno R.

doi:10.1021/acs.orglett.0c02995

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Holmstedt, S., George, L., Koivuporras, A., Valkonen, A., & Candeias, N. R. (2020). Deoxygenative Divergent Synthesis : En Route to Quinic Acid Chirons. Organic Letters, 22(21), 8370-8375. https://doi.org/10.1021/acs.orglett.0c02995

Julkaistu sarjassa

Organic Letters

Tekijät

Holmstedt, Suvi |

George, Lijo |

Koivuporras, Alisa |

Valkonen, Arto |

Candeias, Nuno R.

Päivämäärä

2020

Oppiaine

Orgaaninen kemia Organic Chemistry

Tekijänoikeudet

The installation of vicinal mesylate and silyl ether groups in a quinic acid derivative generates a system prone for stereoselective borane-catalyzed hydrosilylation through a siloxonium intermediate. The diversification of the reaction conditions allowed the construction of different defunctionalized fragments foreseen as useful synthetic fragments. The selectivity of the hydrosilylation was rationalized on the basis of deuteration experiments and computational studies.

Julkaisija

American Chemical Society (ACS)

ISSN Hae Julkaisufoorumista

1523-7060

Rahoittaja(t)

Suomen Akatemia

Rahoitusohjelmat(t)

Akatemiatutkijan tutkimuskulut, SA

Lisätietoja rahoituksesta

The Academy of Finland is duly acknowledged for financial support to N.R.C. (Decisions No. 326487 and 326486) and to A. V. (No. 314343). Finnish Cultural Foundation is acknowledged for financial support to S.H. (00190336).

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