Photocyclization of 4-oxo-4-phenyl-butanoyl amines to δ-lactams

Lindemann, Ute; Reck, G.; Wulff-Molder, Dirk; Wessig, Pablo

doi:10.1016/s0040-4020(98)00002-7

Cited by 33 publications

(12 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Other stereoselective photocyclizations leading to δ‐lactams from 4‐oxo‐4‐phenyl butanoyl amines according to this strategy had previously been reported by Wessig 104a. This author has further extended the methodology to the synthesis of bicyclic β‐turn dipeptides from ( S )‐proline (Scheme ) 104b.…”

Section: 17‐hydrogen‐atom Transfermentioning

confidence: 84%

1,n‐Hydrogen‐Atom Transfer (HAT) Reactions in Which n≠5: An Updated Inventory

Nechab

Mondal

Bertrand

2014

Chemistry A European J

230

View full text Add to dashboard Cite

Hydrogen-atom transfer (HAT) counts amongst the most widely investigated routes to carbon-centered radicals. Intramolecular processes involving 1,5-HAT are widespread to promote regioselective radical "CH activation". The aim of this review is to draw up a comprehensive inventory of the less commonly encountered 1,n-radical translocations (n≠5) with the aim to update this topic with the most recent relevant data.

show abstract

Section: 17‐hydrogen‐atom Transfermentioning

confidence: 84%

1,n‐Hydrogen‐Atom Transfer (HAT) Reactions in Which n≠5: An Updated Inventory

Nechab

Mondal

Bertrand

2014

Chemistry A European J

230

View full text Add to dashboard Cite

show abstract

“…The results can be both drastically increasing (13 and ent-13) and decreasing (2) quantum yields of decay. Furthermore, a very high diastereoselectivity of ring closure can be the consequence as we have described previously [3] [4] [18] [19]. Finally, it should be noted that a-substituted N-acyl-N-methylamino ketones seem to be very suitable reactants for the synthesis of azetidines.…”

Section: Methodsmentioning

confidence: 56%

Enantioselective Preparation of (2R)- and (2S)-Azetidine-2-carboxylic Acids

Wessig

Schwarz

1998

HCA

Self Cite

View full text Add to dashboard Cite

“…70 As previously reported by Wessig and co-workers for achiral γ-ketoamides, 71 unsymmetrically N,N-disubstituted compounds exist as two slowly interconverting amide rotamers. The sterically less demanding methyl group in 57c is E-located in the major conformer as determined by NOE enhancements and the C-C long-range coupling pattern.…”

Section: 6-photocyclizationmentioning

confidence: 60%

Spin-Selectivity in Photochemistry: A Tool for Organic Synthesis

Griesbeck¹

2003

Synlett

View full text Add to dashboard Cite

The photochemistry of carbonyl substrates is largely dependent on the spin multiplicity of the excited state. Singlet and triplet excited carbonyls can differ strongly in chemo-, regio-and stereoselectivity. In bimolecular Paternò-Büchi reactions, both excited singlet and triplets states give rise to oxetane formation, albeit with different selectivities and completely different activation parameters. In unimolecular photocyclizations (Norrish-Yang reaction) the triplet state dominates the reaction. For triplet to singlet intersystem crossing at the biradical level, spin-orbit coupling optimizing geometries are crucial. These geometries are different from classical closed-shell interactions and thus give rise to unusual product stereochemistry as well as unusual concentration and temperature dependences.

show abstract

Photocyclization of 4-oxo-4-phenyl-butanoyl amines to δ-lactams

Cited by 33 publications

References 17 publications

1,n‐Hydrogen‐Atom Transfer (HAT) Reactions in Which n≠5: An Updated Inventory

1,n‐Hydrogen‐Atom Transfer (HAT) Reactions in Which n≠5: An Updated Inventory

Enantioselective Preparation of (2R)- and (2S)-Azetidine-2-carboxylic Acids

Spin-Selectivity in Photochemistry: A Tool for Organic Synthesis

Contact Info

Product

Resources

About