Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate.J Am Chem Soc. 2006 Mar 29; 128(12):3931-3.JA
Abstract
The palladium-catalyzed asymmetric allylic alkylation of a 1:1 mixture of dl- and meso-1,2-divinylethylene carbonate is reported. For the first time, both the ionization and nucleophilic addition steps of the catalytic cycle act as enantiodiscriminating steps to give a single product in high enantiomeric excess. The reactions proceed in >98% ee to efficiently generate useful chiral building blocks from acrolein. The absolute and relative configurations of iso-cladospolide B and 11-epi-iso-cladospolide B were verified by total synthesis, solving an apparent discrepancy in the literature.
Links
MeSH
Pub Type(s)
Journal Article
Research Support, N.I.H., Extramural
Research Support, U.S. Gov't, Non-P.H.S.
Language
eng
PubMed ID
16551099
Citation
Trost, Barry M., and Aaron Aponick. "Palladium-catalyzed Asymmetric Allylic Alkylation of Meso- and Dl-1,2-divinylethylene Carbonate." Journal of the American Chemical Society, vol. 128, no. 12, 2006, pp. 3931-3.
Trost BM, Aponick A. Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate. J Am Chem Soc. 2006;128(12):3931-3.
Trost, B. M., & Aponick, A. (2006). Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate. Journal of the American Chemical Society, 128(12), 3931-3.
Trost BM, Aponick A. Palladium-catalyzed Asymmetric Allylic Alkylation of Meso- and Dl-1,2-divinylethylene Carbonate. J Am Chem Soc. 2006 Mar 29;128(12):3931-3. PubMed PMID: 16551099.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR
T1 - Palladium-catalyzed asymmetric allylic alkylation of meso- and dl-1,2-divinylethylene carbonate.
AU - Trost,Barry M,
AU - Aponick,Aaron,
PY - 2006/3/23/pubmed
PY - 2006/5/26/medline
PY - 2006/3/23/entrez
SP - 3931
EP - 3
JF - Journal of the American Chemical Society
JO - J Am Chem Soc
VL - 128
IS - 12
N2 - The palladium-catalyzed asymmetric allylic alkylation of a 1:1 mixture of dl- and meso-1,2-divinylethylene carbonate is reported. For the first time, both the ionization and nucleophilic addition steps of the catalytic cycle act as enantiodiscriminating steps to give a single product in high enantiomeric excess. The reactions proceed in >98% ee to efficiently generate useful chiral building blocks from acrolein. The absolute and relative configurations of iso-cladospolide B and 11-epi-iso-cladospolide B were verified by total synthesis, solving an apparent discrepancy in the literature.
SN - 0002-7863
UR - https://www.unboundmedicine.com/medline/citation/16551099/Palladium_catalyzed_asymmetric_allylic_alkylation_of_meso__and_dl_12_divinylethylene_carbonate_
DB - PRIME
DP - Unbound Medicine
ER -
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