Nucleophilic participation of phenyl in the ring-opening reactions of cis- and trans-2,3-dibenzyloxirane

Paolo Crotti; Maria Ferretti; Franco Macchia; Annalisa Stoppioni

doi:10.1021/jo00198a024

Nucleophilic participation of phenyl in the ring-opening reactions of cis- and trans-2,3-dibenzyloxirane

The Journal of Organic Chemistry ◽

10.1021/jo00198a024 ◽

1984 ◽

Vol 49 (24) ◽

pp. 4706-4711 ◽

Cited By ~ 7

Author(s):

Paolo Crotti ◽

Maria Ferretti ◽

Franco Macchia ◽

Annalisa Stoppioni

Keyword(s):

Ring Opening ◽

Ring Opening Reactions ◽

Cis And Trans

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ChemInform Abstract: Ring-Opening Reactions of cis- and trans-2,3-Bis(4-methoxybenzyl)oxirane: Competition between Assistance by and Migration of an Aryl Group.

ChemInform ◽

10.1002/chin.198707098 ◽

1987 ◽

Vol 18 (7) ◽

Author(s):

P. CROTTI ◽

M. FERRETTI ◽

F. MACCHIA ◽

A. STOPPIONI

Keyword(s):

Ring Opening ◽

Aryl Group ◽

Ring Opening Reactions ◽

And Migration ◽

Cis And Trans

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Regiochemical Control of the Ring Opening of 1,2-Epoxides by Means of Chelating Processes. 7. Synthesis and Ring-Opening Reactions of cis- and trans-Oxides Derived from 2-(Benzyloxy)-3,6-dihydro-2H-pyran

The Journal of Organic Chemistry ◽

10.1021/jo00094a025 ◽

1994 ◽

Vol 59 (15) ◽

pp. 4131-4137 ◽

Cited By ~ 24

Author(s):

Marco Chini ◽

Paolo Crotti ◽

Cristina Gardelli ◽

Franco Macchia

Keyword(s):

Ring Opening ◽

Ring Opening Reactions ◽

Cis And Trans

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Regiochemical control of the ring opening of 1,2-Epoxides by means of chelating processes. 11. Ring opening reactions of aliphatic mono- and difunctionalized cis and trans 2,3- and 3,4-Epoxy Esters

Tetrahedron ◽

10.1016/0040-4020(95)00877-b ◽

1995 ◽

Vol 51 (48) ◽

pp. 13409-13422 ◽

Cited By ~ 19

Author(s):

Francesca Azzena ◽

Paolo Crotti ◽

Lucilla Favero ◽

Mauro Pineschi

Keyword(s):

Ring Opening ◽

Ring Opening Reactions ◽

Cis And Trans

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ChemInform Abstract: Regiochemical Control of the Ring-Opening of Epoxides by Means of Chelating Processes. Part 13. Synthesis and Ring-Opening Reactions of the Diastereoisomeric cis- and trans-Epoxides Derived from 3-(Benzyloxy)cyclopentene and 2-(Benzyl

ChemInform ◽

10.1002/chin.199848096 ◽

2010 ◽

Vol 29 (48) ◽

pp. no-no

Author(s):

P. CROTTI ◽

V. DI BUSSOLO ◽

L. FAVERO ◽

F. MACCHIA ◽

M. PINESCHI

Keyword(s):

Ring Opening ◽

Ring Opening Reactions ◽

Ring Opening Of Epoxides ◽

Cis And Trans

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ChemInform Abstract: Regiochemical Control of the Ring Opening of 1,2-Epoxides by Means of Chelating Processes. Part 11. Ring Opening Reactions of Aliphatic Mono- and Difunctionalized cis and trans 2,3- and 3,4-Epoxy Esters.

ChemInform ◽

10.1002/chin.199613063 ◽

2010 ◽

Vol 27 (13) ◽

pp. no-no

Author(s):

F. AZZENA ◽

P. CROTTI ◽

L. FAVERO ◽

M. PINESCHI

Keyword(s):

Ring Opening ◽

Ring Opening Reactions ◽

Cis And Trans

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ChemInform Abstract: Regiochemical Control of the Ring Opening of 1,2-Epoxides by Means of Chelating Processes. Part 9. Synthesis and Ring Opening Reactions of cis- and trans-Oxides Derived from 3-(Benzyloxymethyl)cyclopentene and Methyl 2-Cyclopenten-1-c

ChemInform ◽

10.1002/chin.199546064 ◽

2010 ◽

Vol 26 (46) ◽

pp. no-no

Author(s):

M. COLOMBINI ◽

P. CROTTI ◽

V. DI BUSSOLO ◽

L. FAVERO ◽

C. GARDELLI ◽

...

Keyword(s):

Ring Opening ◽

Ring Opening Reactions ◽

Cis And Trans

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Ring-opening reactions of cis- and trans-2,3-bis(4-methoxybenzyl)oxirane: competition between assistance by and migration of anti aryl group

The Journal of Organic Chemistry ◽

10.1021/jo00364a026 ◽

1986 ◽

Vol 51 (14) ◽

pp. 2759-2766 ◽

Cited By ~ 22

Author(s):

Paolo Crotti ◽

Maria Ferretti ◽

Franco Macchia ◽

Annalisa Stoppinoni

Keyword(s):

Ring Opening ◽

Aryl Group ◽

Ring Opening Reactions ◽

And Migration ◽

Cis And Trans

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ChemInform Abstract: Regiochemical Control of the Ring Opening of 1,2-Epoxides by Means of Chelating Processes. Part 8. Synthesis and Ring Opening Reactions of cis- and trans-Oxides Derived from 3-Benzyloxycyclohexene and 2- Benzyloxy-5,6-dihydro-2H-pyran

ChemInform ◽

10.1002/chin.199515076 ◽

2010 ◽

Vol 26 (15) ◽

pp. no-no

Author(s):

F. CALVANI ◽

P. CROTTI ◽

C. GARDELLI ◽

M. PINESCHI

Keyword(s):

Ring Opening ◽

Ring Opening Reactions ◽

Cis And Trans

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Regiochemical control of the ring opening of aziridines by means of chelating processes. 2. Synthesis and ring-opening reactions of aziridines derived from 5,6-dihydro-2H-pyran and of the diastereoisomeric cis- and trans-aziridines derived from 3-(benzyloxy)cyclohexene, 2-(benzyloxy)-3,6-dihydro-, and 2-(benzyloxy)-6-methyl-3,6-dihydro-2H-pyran

Tetrahedron ◽

10.1016/s0040-4020(96)01054-x ◽

1997 ◽

Vol 53 (4) ◽

pp. 1417-1438 ◽

Cited By ~ 16

Author(s):

Paolo Crotti ◽

Valeria Di Bussolo ◽

Lucilla Favero ◽

Mauro Pineschi

Keyword(s):

Ring Opening ◽

Ring Opening Reactions ◽

Cis And Trans

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Aminocyclitols. III. Synthesis of diaminocyclohexanediols

Canadian Journal of Chemistry ◽

10.1139/v79-296 ◽

1979 ◽

Vol 57 (14) ◽

pp. 1870-1876 ◽

Cited By ~ 3

Author(s):

Gerry Kavadias ◽

Robert Droghini

Keyword(s):

Thionyl Chloride ◽

Sodium Azide ◽

Ring Opening ◽

Boron Trifluoride ◽

Boron Trifluoride Etherate ◽

Reaction Sequence ◽

Acidic Hydrolysis ◽

Ring Opening Reactions ◽

Cis And Trans ◽

Hydrolysis Of

Reaction of N,N′-diethoxycarbonyl-2,5-dideoxystreptamine (1b) with thionyl chloride produced the iminoether dihydrochloride 8 which, upon simple treatment with water gave the di-N,O-carbonyl compound 9. Acidic hydrolysis of 9 yielded the aminocyclitol 2a. Alternatively, 2a was prepared from N,N′-dibenzoyl-2,5-dideoxystreptamine (1c) via the oxazoline 10 followed by acidic hydrolysis. Treatment of 1c with triethyl orthoacetate in the presence of boron trifluoride etherate produced the oxazoline 11 and the latter product was hydrolyzed to give 3a. By the same reaction sequence, 1e and 1h were converted to the oxazolines 12 and 13 which upon acidic hydrolysis provided the enantiomeric aminocyclitols 4 and 5. Ring-opening reactions of cis- and trans-1,4-diepoxycyclohexanes (14 and 16) with sodium azide to the diazido compounds 15 and 17, followed by reduction, afforded the aminocyclitols 6 and 7.

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