141041-89-6

Basic information

• Product Name: 3-Oxabicyclo[3.1.0]hexan-2-one, 6-phenyl-, (1S,5R,6S)-
• CAS NO: 141041-89-6
• Molecular Formula: C11H10O2
• Molecular Weight: 174.199
• Mol File: 141041-89-6.mol

Chemical Properties

• CAS DataBase Reference: 3-Oxabicyclo[3.1.0]hexan-2-one, 6-phenyl-, (1S,5R,6S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Oxabicyclo[3.1.0]hexan-2-one, 6-phenyl-, (1S,5R,6S)-(141041-89-6)
• EPA Substance Registry System: 3-Oxabicyclo[3.1.0]hexan-2-one, 6-phenyl-, (1S,5R,6S)-(141041-89-6)

Safety Data

• Hazardous Substances Data: 141041-89-6(Hazardous Substances Data)

Upstream product

• 130780-62-0 cis-3-phenyl-2-propen-1-yl diazoacetate 

Downstream Products

• 130780-69-7 1-(4-morpholinylcarbonyl)-2-(hydroxymethyl)-3-phenylcyclopropane 
• 141506-56-1 ((1S,2R,3S)-2-Hydroxymethyl-3-phenyl-cyclopropyl)-morpholin-4-yl-methanone 
• 141042-73-1 (1R,2R,3R)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarboxylic acid 
• 141042-77-5 (1S,2S,3R)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarboxylic acid 
• 141506-57-2 (1R,2S,3S)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarbaldehyde 
• 141506-58-3 (1S,2S,3S)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarbaldehyde 
• 130780-69-7 ((1R,2R,3S)-2-Hydroxymethyl-3-phenyl-cyclopropyl)-morpholin-4-yl-methanone 
• 141041-99-8 (1R,2R,3S)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarboxylic acid [(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide 
• 141042-02-6 (1S,2S,3S)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarboxylic acid [(S)-1-((1S,2R,3S)-1-cyclohexylmethyl-2,3-dihydroxy-5-methyl-hexylcarbamoyl)-2-thiazol-4-yl-ethyl]-amide 
• 130780-73-3 (1S,2S,3R)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarboxylic acid 
• 130780-73-3 (1S,2S,3S)-2-(Morpholine-4-carbonyl)-3-phenyl-cyclopropanecarboxylic acid 
• 177188-06-6 (S)-((R)-2-Hydroxy-1-phenyl-ethylamino)-[(1R,2R,3R)-2-(morpholine-4-carbonyl)-3-phenyl-cyclopropyl]-acetonitrile 
• 177188-05-5 (R)-((S)-2-Hydroxy-1-phenyl-ethylamino)-[(1R,2R,3R)-2-(morpholine-4-carbonyl)-3-phenyl-cyclopropyl]-acetonitrile 
• 177188-02-2 (S)-((R)-2-Hydroxy-1-phenyl-ethylamino)-[(1S,2R,3R)-2-(morpholine-4-carbonyl)-3-phenyl-cyclopropyl]-acetonitrile 

Relevant articles and documents

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Co(II)-salen-catalyzed asymmetric intramolecular cyclopropanation

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Catalytic Asymmetric Synthesis of Cyclopropane Derivatives with Chiral Ruthenium Complexes: Isolation of Intermediate Carbene Complex

A chiral ruthenium(II)-bis(2-oxazolin-2-yl)pyridine catalyst prepared in situ from optically active bis(2-oxazolin-2-yl)pyridine (Pybox-ip) (2) and [RuCl2(p-cymene)]2 (1) exhibited efficient activity for the asymmetric cyclopropanation (ACP) of styrene and several diazoacetates to give the corresponding trans- and cis-2-phenylcyclopropane-1-carboxylates (3 and 4) in good yields (66-87%). A mixture of 1 and 2 in an atmosphere of ethylene produced the trans-RuCl2(Pybox-ip)(ethylene) complex (5), which also proved to be a powerful catalyst for ACP. The stereoselectivity of the trans- and cis-cyclopropanes were from 90:10 up to 98:2, and their enantioselectivities reached 97%. A catalytic system with 5 could be used for several olefins (6-8) and internal olefins (12 and 13). The non-chiral Ru-Pybox-dihydro catalyst 16 exhibited asymmetric induction with 39% ees of 3 with d- and l-menthyl diazoacetates, and kept a high trans- and cis-stereoselection of 97:3. 2,6-Di-tert-butyl-methylphenyl diazoacetate 17 reacted with the complex 5 to give a stable carbene complex 18, which was characherized by NMR study. The complex 18 exhibited a carbene transfer reaction with styrene at 80°C to give only trans-cyclopropane 3 in 55 %ee.

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Enantioselective intramolecular cyclopropanations of allylic and homoallylic diazoacetates and diazoacetamides using chiral dirhodium(II) carboxamide catalysts

Diazo decomposition of allylic and homoallylic diazoacetates 10a-p and 22a-j catalyzed by chiral dirhodium(II) tetrakis[methyl 2-pyrrolidone-5(S)-carboxylate], Rh2(SS-MEPY)4 (7), and its enantiomer, Rh2(5R-MEPY)4 (8), produces the corresponding intramolecular cyclopropanation products 11a-p and 23a-j in good to excellent yields and with exceptional enantioselectivity. Higher enantiocontrol is observed with allylic diazoacetates than with their homoallylic counterparts, but allylic diazoacetates are subject to greater variations in enantioselectivities with changes in substitution patterns on the carbon-carbon double bond. For example, the enantioselectivities in the intramolecular cyclopropanations of 3-alkyl/aryl-2(Z)-alken-1-yl diazoacetates are generally ≥94%, whereas the cyclizations of the homologous 4-alkyl/aryl-3(Z)-alken-1-yl diazoacetates are typically in the range of 70-90% ee. The corresponding 3-alkyl/aryl-2(E)-alken-1-yl and 4-alkyl/aryl-3(E)-alken-1-yl diazoacetates undergo cyclization with slightly lower ee's (54-85%). Although the Rh2(5S-MEPY)4-catalyzed cyclization of the 2-methallyl diazoacetate 10c proceeds with only 7% ee, alternative chiral dirhodium(II) catalysts, including those with methyl N-acylimidazolidin-2-one-4(5)-carboxylate ligands such as Rh2(4S-MACIM)4 (14) and Rh2(4S-MPAIM)4 (15), may be employed to increase the level of enantiocontrol to 78 and 65%, respectively. Some allylic diazoacetamides also undergo highly enantioselective cyclization to form cyclopropyl lactams as illustrated by the diazo decomposition of N-allyl diazoacetamide (19) in the presence of dirhodium(II) tetrakis[methyl 2-oxazolidinone-4(S)-carboxylate], Rh2(4S-MEOX)4, to give the 3-azabicyclo[3.1.0]hexan-2-one 20 in 98% ee. The absolute configuration and the level of enantiocontrol in these intramolecular cyclopropanations have been interpreted by a transition state model in which the important determinants are (i) the preferred conformation about the rhodium-carbon bond; (ii) the trajectory of approach of the double bond to the metallocarbene center; and (iii) the orientation of the double bond with respect to the chiral face of the catalyst.