The Preparation of Single Enantiomer 2-Naphthylalanine Derivatives Using Rhodium−Methyl BoPhoz-catalyzed Asymmetric Hydrogenation
Neil W Boaz
1
,
Shannon E Large
1
,
James A Ponasik
1
,
Mary K Moore
1
,
Theresa Barnette
1
,
W Dell Nottingham
1
1
Research Laboratories, Eastman Chemical Company, Kingsport, Tennessee 37662, U.S.A.
|
Publication type: Journal Article
Publication date: 2005-05-24
scimago Q1
wos Q1
SJR: 0.865
CiteScore: 5.4
Impact factor: 3.5
ISSN: 10836160, 1520586X
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
The single enantiomers of 2-naphthylalanine and N-tert-butoxycarbonyl 2-naphthylalanine were prepared from 2-naphthaldehyde. The sequence has been optimized and run on multikilogram scale, with the key step the asymmetric hydrogenation of methyl 2-acetamido-3-(2-naphthyl)propenoate using the rhodium complex of the methyl BoPhoz ligand, which proceeded smoothly at scale with 97.9% ee. Enhancement to >99.5% ee was achieved by crystallization of the methyl 2-amino-3-(2-naphthyl)propanoate methanesulfonic acid addition salt, the product of acidic deacylation of the hydrogenation product. This protocol for enantiomeric purity enhancement appears to be general for these types of amino acid derivatives. Subsequent transformations did not effect the enantiomeric purity, affording the desired products in >99.5% ee.
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Boaz N. W. et al. The Preparation of Single Enantiomer 2-Naphthylalanine Derivatives Using Rhodium−Methyl BoPhoz-catalyzed Asymmetric Hydrogenation // Organic Process Research and Development. 2005. Vol. 9. No. 4. pp. 472-478.
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Boaz N. W., Large S. E., Ponasik J. A., Moore M. K., Barnette T., Nottingham W. D. The Preparation of Single Enantiomer 2-Naphthylalanine Derivatives Using Rhodium−Methyl BoPhoz-catalyzed Asymmetric Hydrogenation // Organic Process Research and Development. 2005. Vol. 9. No. 4. pp. 472-478.
Cite this
RIS
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TY - JOUR
DO - 10.1021/op050026g
UR - https://doi.org/10.1021/op050026g
TI - The Preparation of Single Enantiomer 2-Naphthylalanine Derivatives Using Rhodium−Methyl BoPhoz-catalyzed Asymmetric Hydrogenation
T2 - Organic Process Research and Development
AU - Boaz, Neil W
AU - Large, Shannon E
AU - Ponasik, James A
AU - Moore, Mary K
AU - Barnette, Theresa
AU - Nottingham, W Dell
PY - 2005
DA - 2005/05/24
PB - American Chemical Society (ACS)
SP - 472-478
IS - 4
VL - 9
SN - 1083-6160
SN - 1520-586X
ER -
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BibTex (up to 50 authors)
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@article{2005_Boaz,
author = {Neil W Boaz and Shannon E Large and James A Ponasik and Mary K Moore and Theresa Barnette and W Dell Nottingham},
title = {The Preparation of Single Enantiomer 2-Naphthylalanine Derivatives Using Rhodium−Methyl BoPhoz-catalyzed Asymmetric Hydrogenation},
journal = {Organic Process Research and Development},
year = {2005},
volume = {9},
publisher = {American Chemical Society (ACS)},
month = {may},
url = {https://doi.org/10.1021/op050026g},
number = {4},
pages = {472--478},
doi = {10.1021/op050026g}
}
Cite this
MLA
Copy
Boaz, Neil W., et al. “The Preparation of Single Enantiomer 2-Naphthylalanine Derivatives Using Rhodium−Methyl BoPhoz-catalyzed Asymmetric Hydrogenation.” Organic Process Research and Development, vol. 9, no. 4, May. 2005, pp. 472-478. https://doi.org/10.1021/op050026g.