Journal of the American Chemical Society, volume 132, issue 13, pages 4562-4563
anti-Diastereo- and enantioselective carbonyl (hydroxymethyl)allylation from the alcohol or aldehyde oxidation level: allyl carbonates as allylmetal surrogates.
Publication type: Journal Article
Publication date: 2010-03-12
Q1
Q1
SJR: 5.489
CiteScore: 24.4
Impact factor: 14.4
ISSN: 00027863, 15205126
PubMed ID:
20225853
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Enantioselective transfer hydrogenation of carbonate 1a in the presence of aromatic, allylic, or aliphatic alcohols 2a-2i employing a cyclometalated iridium C,O-benzoate derived from allyl acetate, 4-cyano-3-nitrobenzoic acid and (S)-SEGPHOS delivers products of (hydroxymethyl)allylation 4a-4i in good isolated yields (60-74%), good anti-diastereoselectivities (5:1-10:1 dr) and exceptional levels of enantiocontrol (93-99% ee). Under identical reaction conditions, but in the presence of isopropanol, aldehydes 3a-3i are converted to an equivalent set of adducts 4a-4i in good isolated yields (58-74%), good anti-diastereoselectivities (4:1-14:1 dr), and exceptional levels of enantiocontrol (95-99% ee). Thus, identical sets of adducts 4a-4i are produced with equal facility from the alcohol or aldehyde oxidation level. These studies represent the first general method for enantioselective carbonyl (hydroxymethyl)allylation, a process that has no highly stereoselective counterpart in conventional allylmetal chemistry.
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Zhang Y. J. et al. anti-Diastereo- and enantioselective carbonyl (hydroxymethyl)allylation from the alcohol or aldehyde oxidation level: allyl carbonates as allylmetal surrogates. // Journal of the American Chemical Society. 2010. Vol. 132. No. 13. pp. 4562-4563.
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Zhang Y. J., Yang J. H., Kim S., Krische M. J. anti-Diastereo- and enantioselective carbonyl (hydroxymethyl)allylation from the alcohol or aldehyde oxidation level: allyl carbonates as allylmetal surrogates. // Journal of the American Chemical Society. 2010. Vol. 132. No. 13. pp. 4562-4563.
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TY - JOUR
DO - 10.1021/ja100949e
UR - https://doi.org/10.1021/ja100949e
TI - anti-Diastereo- and enantioselective carbonyl (hydroxymethyl)allylation from the alcohol or aldehyde oxidation level: allyl carbonates as allylmetal surrogates.
T2 - Journal of the American Chemical Society
AU - Zhang, Yong Jian
AU - Yang, Jin Haek
AU - Kim, Sang-Hoon
AU - Krische, Michael J
PY - 2010
DA - 2010/03/12
PB - American Chemical Society (ACS)
SP - 4562-4563
IS - 13
VL - 132
PMID - 20225853
SN - 0002-7863
SN - 1520-5126
ER -
Cite this
BibTex (up to 50 authors)
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@article{2010_Zhang,
author = {Yong Jian Zhang and Jin Haek Yang and Sang-Hoon Kim and Michael J Krische},
title = {anti-Diastereo- and enantioselective carbonyl (hydroxymethyl)allylation from the alcohol or aldehyde oxidation level: allyl carbonates as allylmetal surrogates.},
journal = {Journal of the American Chemical Society},
year = {2010},
volume = {132},
publisher = {American Chemical Society (ACS)},
month = {mar},
url = {https://doi.org/10.1021/ja100949e},
number = {13},
pages = {4562--4563},
doi = {10.1021/ja100949e}
}
Cite this
MLA
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Zhang, Yong Jian, et al. “anti-Diastereo- and enantioselective carbonyl (hydroxymethyl)allylation from the alcohol or aldehyde oxidation level: allyl carbonates as allylmetal surrogates..” Journal of the American Chemical Society, vol. 132, no. 13, Mar. 2010, pp. 4562-4563. https://doi.org/10.1021/ja100949e.