Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/15940
Title: Enantioselective tandem conjugate addition-elimination reactions
Authors: XU JUNYE
Keywords: enantioselective, tandem, conjugate addition-elimination, allylic bromide, chiral pyrrolidinyl sulfonamide, Baylis-Hillman
Issue Date: 9-May-2009
Source: XU JUNYE (2009-05-09). Enantioselective tandem conjugate addition-elimination reactions. ScholarBank@NUS Repository.
Abstract: Chiral pyrrolidinyl sulfonamides (CPS) were easily synthesized from commerically available chiral amino alcohols. In 3 steps, the CPS can be obtained in multigram quantity and high yields. Tandem conjugate addition-elimination (CA-E) reactions between Morita-Baylis-Hillman (MBH) allylic bromides and 1,3-dicarbonyl compounds were investigated in the presence of various CPSs. Moderate to high yields (up to 97%) and high enantioselectivities (up to 98% ee) were achieved with stoichiometric CPS. The CPS can be easily recovered through an acid-base workup and reused without loss of activity.When amine or phosphorus donor was employed as the nucleophile, only moderate yield was obtained accompanied with moderate to good enantioselectivity. The highly functionalized products can be used to generate a variety of interesting enantiomerically pure compounds via simple transformations. Polystyrene-supported chiral pyrrolidinyl sulfonamide (PS-CPS) was also prepared and utilized for the tandem CA-E reactions.
URI: http://scholarbank.nus.edu.sg/handle/10635/15940
Appears in Collections:Ph.D Theses (Open)

Show full item record
Files in This Item:
File Description SizeFormatAccess SettingsVersion 
1 Cover.pdf7.13 kBAdobe PDF

OPEN

NoneView/Download
2 title page.pdf10.33 kBAdobe PDF

OPEN

NoneView/Download
3 Contents.pdf87.27 kBAdobe PDF

OPEN

NoneView/Download
4 Chapter 1 Intro.pdf121.1 kBAdobe PDF

OPEN

NoneView/Download
5 Chapter 2 cyclic.pdf297.75 kBAdobe PDF

OPEN

NoneView/Download
6 Chapter 3 Linear.pdf72.16 kBAdobe PDF

OPEN

NoneView/Download
7 Chapter 4 BH.pdf154.94 kBAdobe PDF

OPEN

NoneView/Download
8 Chapter 5 Exp.pdf290.22 kBAdobe PDF

OPEN

NoneView/Download
9 Appendices copies of NMR and X-ray.pdf1.08 MBAdobe PDF

OPEN

NoneView/Download
10 Publications.pdf8.46 kBAdobe PDF

OPEN

NoneView/Download

Page view(s)

262
checked on Dec 2, 2017

Download(s)

1,805
checked on Dec 2, 2017

Google ScholarTM

Check


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.