Synthesis of Novel Picolylamine Template Catalysts and its Applications in Asymmetric Aldol Reactions

  • A pyridine based 1,2-diamine containing only one stereogenic center has been identified for fast aldol reactions (16-48h). Using 2-5 mol% of (R)- or (S)-PicAm-2a, cyclohexanone (3.3 equiv) readily undergoes aldol reactions with o-,m- p-substituted aromatic aldehyde partners (limiting reagents), including the poor electrophile 4-methylbenzaldehyde (95-99% ee). Further more, functionalized cyclic ketone substrates have been converted into four aldol products using the lowest catalyst loading (5.0 mol%) to date with the highest yield and enatioselectivity.

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Publishing Institution:IRC-Library, Information Resource Center der Jacobs University Bremen
Granting Institution:Jacobs Univ.
Author:Muhammad Naveed Umar
Referee:Thomas Nugent, Nikolai Kuhnert, Zia-Ur- Rehman
Advisor:Thomas Nugent
Persistent Identifier (URN):urn:nbn:de:101:1-2013052411269
Document Type:PhD Thesis
Date of Successful Oral Defense:2010/09/29
Date of First Publication:2010/10/06
PhD Degree:Chemistry
School:SES School of Engineering and Science
Library of Congress Classification:Q Science / QD Chemistry / QD241-441 Organic chemistry
Call No:Thesis 2010/22

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