2001
DOI: 10.1039/b008866h
|View full text |Cite
|
Sign up to set email alerts
|

Highly diastereoselective synthesis of 1,3-oxazolidines under thermodynamic control using focused microwave irradiation under solvent-free conditions

Abstract: A number of 1,3-oxazolidines, derived from enantiomerically pure amino alcohols such as (2)-ephedrine and (+)-pseudoephedrine, have been synthesised under solvent-free conditions using a focused microwave reactor. The condensation reaction between the amino alcohol and an aldehyde yields 1,3-oxazolidines in excellent yields and diastereoselectivities. Prolonged microwave irradiation increases the diastereoselectivity of the reaction and produces the thermodynamically more stable diastereomer. JHC This journal … Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
2
1
1

Citation Types

0
15
0
1

Year Published

2002
2002
2012
2012

Publication Types

Select...
7
2

Relationship

2
7

Authors

Journals

citations
Cited by 32 publications
(16 citation statements)
references
References 20 publications
0
15
0
1
Order By: Relevance
“…Whereas in homogenous reactions under microwave conditions, the selectivity essentially follows the thermal pattern, [25] it seems to be possible to alter the selectivity in heterogeneous reactions.…”
Section: Discussionmentioning
confidence: 99%
“…Whereas in homogenous reactions under microwave conditions, the selectivity essentially follows the thermal pattern, [25] it seems to be possible to alter the selectivity in heterogeneous reactions.…”
Section: Discussionmentioning
confidence: 99%
“…3,4S‐Dimethyl‐2S,5R‐diphenyl‐oxazolidine 4 15–20. (1R,2S)‐(−)‐2‐Methylamino‐1‐phenyl‐1‐propanol (2.06 g, 12.5 mmol) and freshly distilled benzaldehyde (1.32 g, 12.5 mmol) were dissolved in anhydrous toluene (30 mL).…”
Section: Methodsmentioning
confidence: 99%
“…The development and use of ionic liquids have emerged as a fascinating technology because, in addition to their negligible vapor pressure and recyclability, they present unique physicochemical properties such as tunable polarity, high thermal stability and miscibility with a number of organic solvents [1,2]. With regard to alternative energy sources, the use of microwave ovens for synthesis has been accepted as a way of reducing reaction times, often by orders of magnitude, and of increasing product yields when compared to conventional methods [3,4]. A key advantage of modern scientific microwave equipment is the ability to control very specific reaction conditions, monitoring temperature, pressure, and reaction times.…”
Section: Introductionmentioning
confidence: 99%