Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer
Тип публикации: Journal Article
Дата публикации: 1991-05-01
scimago Q1
wos Q1
БС1
SJR: 5.489
CiteScore: 24.4
Impact factor: 15.6
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Краткое описание
The chromium(II)-mediated addition («Hiyama reaction») of the chiral allylic bromides to achiral and chiral aldehydes proceeds with high Felkin-Anh selectivity with respect to the stereocenter at Cγ in the bromide (Table II). By double stereodifferentiation experiments (Tables III/IV) it was shown that the bromide is the stereodominating component in the addition. The methodology was applied to the first synthesis of nephromopsinic acid (−) found in the lichen species nephromopsis stracheyi, and its enantiomer
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Mulzer J. et al. Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer // Journal of the American Chemical Society. 1991. Vol. 113. No. 11. pp. 4218-4229.
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Mulzer J., Kattner L., Strecker A. R., Schröder C., Buschmann J., Lehmann C., Luger P. Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer // Journal of the American Chemical Society. 1991. Vol. 113. No. 11. pp. 4218-4229.
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TY - JOUR
DO - 10.1021/ja00011a025
UR - https://doi.org/10.1021/ja00011a025
TI - Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer
T2 - Journal of the American Chemical Society
AU - Mulzer, Johann
AU - Kattner, Lars
AU - Strecker, Achim R.
AU - Schröder, Christian
AU - Buschmann, Juergen
AU - Lehmann, Christian
AU - Luger, Peter
PY - 1991
DA - 1991/05/01
PB - American Chemical Society (ACS)
SP - 4218-4229
IS - 11
VL - 113
SN - 0002-7863
SN - 1520-5126
ER -
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@article{1991_Mulzer,
author = {Johann Mulzer and Lars Kattner and Achim R. Strecker and Christian Schröder and Juergen Buschmann and Christian Lehmann and Peter Luger},
title = {Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer},
journal = {Journal of the American Chemical Society},
year = {1991},
volume = {113},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/ja00011a025},
number = {11},
pages = {4218--4229},
doi = {10.1021/ja00011a025}
}
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MLA
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Mulzer, Johann, et al. “Highly Felkin-Anh selective Hiyama additions of chiral allylic bromides to aldehydes. Application to the first synthesis of nephromopsinic acid and its enantiomer.” Journal of the American Chemical Society, vol. 113, no. 11, May. 1991, pp. 4218-4229. https://doi.org/10.1021/ja00011a025.