Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols
- Authors
- Lee, Jaeyong; Ban, Jeong Woo; Kim, Jeongseok; Yang, Sehun; Lee, Geumwoo; Dhorma, Lama Prema; Kim, Mi-hyun; Ha, Min Woo; Hong, Suckchang; Park, Hyeung-geun
- Issue Date
- 4-Mar-2022
- Publisher
- AMER CHEMICAL SOC
- Citation
- ORGANIC LETTERS, v.24, no.8, pp.1647 - 1651
- Journal Title
- ORGANIC LETTERS
- Volume
- 24
- Number
- 8
- Start Page
- 1647
- End Page
- 1651
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/83935
- DOI
- 10.1021/acs.orglett.2c00192
- ISSN
- 1523-7060
- Abstract
- The highly enantioselective aza-Michael reaction of tert-butyl beta-naphthylmetlioxycarbamate 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 degrees 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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