Seebach's oxazolidinone is a good catalyst for aldol reactions: Tetrahedron Lett.

Carles Isart; Jordi Bures; Jaume Vilarrasa

Seebach's oxazolidinone is a good catalyst for aldol reactions: Tetrahedron Lett.

Carles Isart
, Jordi Bures
, Jaume Vilarrasa

Research output: Contribution to journal › Article › peer-review

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Abstract

Seebach's proline-derived oxazolidinone I overcomes (S)-proline and is at least as efficient as (S)-5-(pyrrolidin-2-yl)tetrazole in several organocatalytic aldol reactions examd. A quick exchange takes place between I and carbonyl compds. that gives bicyclic oxazolidinones, in equil. with the very minor active species (enamines). Maximum yields of the aldols (beta -hydroxy ketones) were achieved after 1-4 h when, with proline, they are attained after 30-48 h.

Original language	English
Pages (from-to)	5414-5418
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Publication status	Published - 2008

Keywords

Aldol addition catalysts Stereoselective synthesis (stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes) Aldol addition (stereoselective stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes) hydroxyketone asym prepn ketone aldehyde asym aldol addn oxazolidinone oxazolidinone asym aldol addn catalyst

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Isart-2008-Seebach's oxazolidin

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Isart, C., Bures, J., & Vilarrasa, J. (2008). Seebach's oxazolidinone is a good catalyst for aldol reactions: Tetrahedron Lett. Tetrahedron Letters, 49, 5414-5418. http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6THS-4SXH9WV-8-P&_cdi=5290&_user=1018416&_pii=S004040390801277X&_orig=search&_coverDate=09%2F08%2F2008&_sk=999509962&view=c&wchp=dGLbVtb-zSkzV&md5=dda40b800ebf7b4386fb26c1698ab434&ie=/sdarticle.pdf

@article{1d7a53605eb449d0963414bc235f97e0,

title = "Seebach's oxazolidinone is a good catalyst for aldol reactions: Tetrahedron Lett.",

abstract = "Seebach's proline-derived oxazolidinone I overcomes (S)-proline and is at least as efficient as (S)-5-(pyrrolidin-2-yl)tetrazole in several organocatalytic aldol reactions examd. A quick exchange takes place between I and carbonyl compds. that gives bicyclic oxazolidinones, in equil. with the very minor active species (enamines). Maximum yields of the aldols (beta -hydroxy ketones) were achieved after 1-4 h when, with proline, they are attained after 30-48 h.",

keywords = "Aldol addition catalysts Stereoselective synthesis (stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes) Aldol addition (stereoselective stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes) hydroxyketone asym prepn ketone aldehyde asym aldol addn oxazolidinone oxazolidinone asym aldol addn catalyst",

author = "Carles Isart and Jordi Bures and Jaume Vilarrasa",

note = "M1 - 37 CAN 149:401924 Aliphatic Compounds 81286-82-0 Role: CAT (Catalyst use), RCT (Reactant), USES (Uses), RACT (Reactant or reagent) (stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes); 67-64-1 (Acetone); 100-52-7 (Benzaldehyde); 108-94-1 (Cyclohexanone); 116-09-6; 147-85-3 (L-Proline); 555-16-8 (4-Nitrobenzaldehyde); 630-19-3; 2043-61-0 (Cyclohexanecarboxaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes); 86734-67-0P; 117772-78-8P; 264224-65-9P; 293297-60-6P; 351533-35-2P; 704905-36-2P; 704905-48-6P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes)",

year = "2008",

language = "English",

volume = "49",

pages = "5414--5418",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier BV",

}

Isart, C, Bures, J & Vilarrasa, J 2008, 'Seebach's oxazolidinone is a good catalyst for aldol reactions: Tetrahedron Lett.', Tetrahedron Letters, vol. 49, pp. 5414-5418. <http://www.sciencedirect.com/science?_ob=MImg&_imagekey=B6THS-4SXH9WV-8-P&_cdi=5290&_user=1018416&_pii=S004040390801277X&_orig=search&_coverDate=09%2F08%2F2008&_sk=999509962&view=c&wchp=dGLbVtb-zSkzV&md5=dda40b800ebf7b4386fb26c1698ab434&ie=/sdarticle.pdf>

TY - JOUR

T1 - Seebach's oxazolidinone is a good catalyst for aldol reactions

T2 - Tetrahedron Lett.

AU - Isart, Carles

AU - Bures, Jordi

AU - Vilarrasa, Jaume

N1 - M1 - 37 CAN 149:401924 Aliphatic Compounds 81286-82-0 Role: CAT (Catalyst use), RCT (Reactant), USES (Uses), RACT (Reactant or reagent) (stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes); 67-64-1 (Acetone); 100-52-7 (Benzaldehyde); 108-94-1 (Cyclohexanone); 116-09-6; 147-85-3 (L-Proline); 555-16-8 (4-Nitrobenzaldehyde); 630-19-3; 2043-61-0 (Cyclohexanecarboxaldehyde) Role: RCT (Reactant), RACT (Reactant or reagent) (stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes); 86734-67-0P; 117772-78-8P; 264224-65-9P; 293297-60-6P; 351533-35-2P; 704905-36-2P; 704905-48-6P Role: SPN (Synthetic preparation), PREP (Preparation) (stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes)

PY - 2008

Y1 - 2008

N2 - Seebach's proline-derived oxazolidinone I overcomes (S)-proline and is at least as efficient as (S)-5-(pyrrolidin-2-yl)tetrazole in several organocatalytic aldol reactions examd. A quick exchange takes place between I and carbonyl compds. that gives bicyclic oxazolidinones, in equil. with the very minor active species (enamines). Maximum yields of the aldols (beta -hydroxy ketones) were achieved after 1-4 h when, with proline, they are attained after 30-48 h.

AB - Seebach's proline-derived oxazolidinone I overcomes (S)-proline and is at least as efficient as (S)-5-(pyrrolidin-2-yl)tetrazole in several organocatalytic aldol reactions examd. A quick exchange takes place between I and carbonyl compds. that gives bicyclic oxazolidinones, in equil. with the very minor active species (enamines). Maximum yields of the aldols (beta -hydroxy ketones) were achieved after 1-4 h when, with proline, they are attained after 30-48 h.

KW - Aldol addition catalysts Stereoselective synthesis (stereoselective prepn. of hydroxyketones via Seebach's oxazolidinone-catalyzed asym. aldol addn. of ketones with aldehydes) Aldol addition (stereoselective stereoselective prepn. of hydroxyketones via Se

M3 - Article

SN - 0040-4039

VL - 49

SP - 5414

EP - 5418

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

Seebach's oxazolidinone is a good catalyst for aldol reactions: Tetrahedron Lett.

Abstract

Keywords

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