Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols
Jaeyong Lee
1
,
Jeong Woo Ban
1
,
Jeongseok Kim
1
,
Sehun Yang
1
,
Geumwoo Lee
1
,
Lama Prema Dhorma
2
,
Mi Hyun Kim
2
,
Min-Woo Ha
3
,
Suckchang Hong
1
,
Hyeung-Geun Park
1
2
Publication type: Journal Article
Publication date: 2022-02-17
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
35175781
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
The highly enantioselective aza-Michael reaction of tert-butyl β-naphthylmethoxycarbamate to cyclic enones has been accomplished by using a new cinchona alkaloid derived C(9)-urea ammonium catalyst under phase-transfer catalysis conditions with up to 98% ee at 0 °C. The resulting aza-Michael adducts can be converted to versatile intermediates by selective deprotection and the cyclic 1,3-aminoalcohols by diastereoselective reduction with up to 32:1, which have been widely used as important pharmacophores in pharmaceutical development.
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8
Total citations:
8
Citations from 2025:
2
(25%)
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GOST
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Lee J. et al. Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols // Organic Letters. 2022. Vol. 24. No. 8. pp. 1647-1651.
GOST all authors (up to 50)
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Lee J., Ban J. W., Kim J., Yang S., Lee G., Dhorma L. P., Kim M. H., Ha M., Hong S., Park H. Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols // Organic Letters. 2022. Vol. 24. No. 8. pp. 1647-1651.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.2c00192
UR - https://doi.org/10.1021/acs.orglett.2c00192
TI - Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols
T2 - Organic Letters
AU - Lee, Jaeyong
AU - Ban, Jeong Woo
AU - Kim, Jeongseok
AU - Yang, Sehun
AU - Lee, Geumwoo
AU - Dhorma, Lama Prema
AU - Kim, Mi Hyun
AU - Ha, Min-Woo
AU - Hong, Suckchang
AU - Park, Hyeung-Geun
PY - 2022
DA - 2022/02/17
PB - American Chemical Society (ACS)
SP - 1647-1651
IS - 8
VL - 24
PMID - 35175781
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2022_Lee,
author = {Jaeyong Lee and Jeong Woo Ban and Jeongseok Kim and Sehun Yang and Geumwoo Lee and Lama Prema Dhorma and Mi Hyun Kim and Min-Woo Ha and Suckchang Hong and Hyeung-Geun Park},
title = {Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols},
journal = {Organic Letters},
year = {2022},
volume = {24},
publisher = {American Chemical Society (ACS)},
month = {feb},
url = {https://doi.org/10.1021/acs.orglett.2c00192},
number = {8},
pages = {1647--1651},
doi = {10.1021/acs.orglett.2c00192}
}
Cite this
MLA
Copy
Lee, Jaeyong, et al. “Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols.” Organic Letters, vol. 24, no. 8, Feb. 2022, pp. 1647-1651. https://doi.org/10.1021/acs.orglett.2c00192.