Stereoselective allylation of α-hydroxy aldimines and its application to the formal synthesis of (−)-β-conhydrine. Issue 4 (25th January 2018)
- Record Type:
- Journal Article
- Title:
- Stereoselective allylation of α-hydroxy aldimines and its application to the formal synthesis of (−)-β-conhydrine. Issue 4 (25th January 2018)
- Main Title:
- Stereoselective allylation of α-hydroxy aldimines and its application to the formal synthesis of (−)-β-conhydrine
- Authors:
- Lee, Yong-Taek
Jung, Changyoung
Myeong, In-Soo
Lee, Sang-Hyun
Kim, Jin-Seok
Ham, Won-Hun - Abstract:
- Abstract: Stereoselective allylation of N - p -methoxyphenyl (PMP)-substituted α-hydroxy aldimines is described. Several Lewis acids (BF3 ·OEt2, SnCl4, TiCl4, ZnCl2, and MgBr2 ·OEt2 ) were employed to mediate the allylation reactions. The addition of the allyl group generates a new stereocenter and affords the syn vicinal amino alcohol. Formal synthesis of (−)-β-conhydrine (1 ) was accomplished via syn -selective allyl addition to N -PMP-substituted α-hydroxy aldimine. Graphical abstract:
- Is Part Of:
- Tetrahedron. Volume 74:Issue 4(2018)
- Journal:
- Tetrahedron
- Issue:
- Volume 74:Issue 4(2018)
- Issue Display:
- Volume 74, Issue 4 (2018)
- Year:
- 2018
- Volume:
- 74
- Issue:
- 4
- Issue Sort Value:
- 2018-0074-0004-0000
- Page Start:
- 506
- Page End:
- 511
- Publication Date:
- 2018-01-25
- Subjects:
- (‒)-β-Conhydrine -- α-Hydroxy aldimines -- Stereoselective allylation -- Vicinal amino alcohol
Chemistry, Organic -- Periodicals
547.005 - Journal URLs:
- http://www.elsevier.com/journals ↗
- DOI:
- 10.1016/j.tet.2017.12.024 ↗
- Languages:
- English
- ISSNs:
- 0040-4020
- Deposit Type:
- Legaldeposit
- View Content:
- Available online (eLD content is only available in our Reading Rooms) ↗
- Physical Locations:
- British Library DSC - 8796.850000
British Library DSC - BLDSS-3PM
British Library STI - ELD Digital store - Ingest File:
- 5580.xml