Design and synthesis of a new polymer-supported Evans-type oxazolidinone: An efficient chiral auxiliary in the solid-ph ase asymmetric alkylation reactions

34Citations
Citations of this article
14Readers
Mendeley users who have this article in their library.
Get full text

Abstract

Wang resin-supported Evans' chiral auxiliary (23) was designed based on a novel polymer-anchoring strategy, which utilizes the 5-position of the oxazolidinone ring, and its new synthetic route applicable to multi-gram preparation in just a day was developed. Solid-phase Evans' asymmetric alkylation on 23-derived N-acylimide resin and following lithium hydroperoxide-mediated chemoselective hydrolysis afforded the corresponding α-branched carboxylic acids in desired high stereoselectivities (up to 97% ee) and moderate to good overall yield (up to 70%, for 3 steps), which were comparable to those of the conventional solution-phase methods. Furthermore, recovery and recycling of the polymer-supported chiral auxiliary were successfully achieved without decreasing the stereoselectivity of the product. Therefore, this is the first successful example that the solid-phase Evans' asymmetric enolate-alkylation was efficiently performed on the solid-support, and it is concluded that the connection to the solid-support via the 5-position of the oxazolidinone ring is an ideal strategy in the solid-phase Evans' chiral auxiliary. © 2005 Elsevier Ltd. All rights reserved.

References Powered by Scopus

Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides

3628Citations
N/AReaders
Get full text

Eine neue Methode zur Synthese von Peptiden: Aktivierung der Carboxylgruppe mit Dicyclohexylcarbodiimid unter Zusatz von 1‐Hydroxy‐benzotriazolen

1928Citations
N/AReaders
Get full text

1,2-Amino alcohols and their heterocyclic derivatives as chiral auxiliaries in asymmetric synthesis

1724Citations
N/AReaders
Get full text

Cited by Powered by Scopus

The state of the art in asymmetric induction: the aldol reaction as a case study

207Citations
N/AReaders
Get full text

Comprehensive survey of combinatorial library synthesis: 2005

113Citations
N/AReaders
Get full text

Oxazolidin-2-one ring, a popular framework in synthetic organic chemistry: Part 1. The construction of the oxazolidin-2-one ring

73Citations
N/AReaders
Get full text

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Cite

CITATION STYLE

APA

Kotake, T., Hayashi, Y., Rajesh, S., Mukai, Y., Takiguchi, Y., Kimura, T., & Kiso, Y. (2005). Design and synthesis of a new polymer-supported Evans-type oxazolidinone: An efficient chiral auxiliary in the solid-ph ase asymmetric alkylation reactions. Tetrahedron, 61(15), 3819–3833. https://doi.org/10.1016/j.tet.2005.01.135

Readers' Seniority

Tooltip

PhD / Post grad / Masters / Doc 4

50%

Researcher 3

38%

Professor / Associate Prof. 1

13%

Readers' Discipline

Tooltip

Chemistry 3

43%

Agricultural and Biological Sciences 2

29%

Pharmacology, Toxicology and Pharmaceut... 1

14%

Social Sciences 1

14%

Save time finding and organizing research with Mendeley

Sign up for free