Synthesis of 3-Azabicyclo[3.3.0]octane Framework and a Novel Tricyclicaminoether

H. Ümit Kaniskan; Özdemir Dogan

doi:10.1081/SCC-120025195

Synthesis of 3-Azabicyclo[3.3.0]octane Framework and a Novel Tricyclicaminoether

H. Ümit Kaniskan, Özdemir Dogan

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

1 Scopus citations

Abstract

The efficient synthesis of 3-azabicyclo [3.3.0]octane derivative 1 and a novel tricyclicaminoether 11 has been achieved in seven steps using commercially available starting materials and commonly used reagents. The key steps are the intramolecular ring opening of epoxide 7 providing tricyclic aminoalcohol 3 and Baeyer-Villiger oxidation of ketone 8 providing the corresponding lactone 2. Both reactions proceeded regiospecifically.

Original language	English
Pages (from-to)	3833-3841
Number of pages	9
Journal	Synthetic Communications
Volume	33
Issue number	21
DOIs	https://doi.org/10.1081/SCC-120025195
State	Published - 2003
Externally published	Yes

Keywords

Baeyer-Villiger oxidation
Cage-like oxaheterocycle
Intramolecular cyclization
Tricyclicaminoether

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10.1081/SCC-120025195

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title = "Synthesis of 3-Azabicyclo[3.3.0]octane Framework and a Novel Tricyclicaminoether",

abstract = "The efficient synthesis of 3-azabicyclo [3.3.0]octane derivative 1 and a novel tricyclicaminoether 11 has been achieved in seven steps using commercially available starting materials and commonly used reagents. The key steps are the intramolecular ring opening of epoxide 7 providing tricyclic aminoalcohol 3 and Baeyer-Villiger oxidation of ketone 8 providing the corresponding lactone 2. Both reactions proceeded regiospecifically.",

keywords = "Baeyer-Villiger oxidation, Cage-like oxaheterocycle, Intramolecular cyclization, Tricyclicaminoether",

author = "Kaniskan, {H. {\"U}mit} and {\"O}zdemir Dogan",

note = "Funding Information: We thank the Middle East Technical University Research Foundation for the financial support.",

year = "2003",

doi = "10.1081/SCC-120025195",

language = "English",

volume = "33",

pages = "3833--3841",

journal = "Synthetic Communications",

issn = "0039-7911",

publisher = "Taylor and Francis Ltd.",

number = "21",

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TY - JOUR

T1 - Synthesis of 3-Azabicyclo[3.3.0]octane Framework and a Novel Tricyclicaminoether

AU - Kaniskan, H. Ümit

AU - Dogan, Özdemir

N1 - Funding Information: We thank the Middle East Technical University Research Foundation for the financial support.

PY - 2003

Y1 - 2003

N2 - The efficient synthesis of 3-azabicyclo [3.3.0]octane derivative 1 and a novel tricyclicaminoether 11 has been achieved in seven steps using commercially available starting materials and commonly used reagents. The key steps are the intramolecular ring opening of epoxide 7 providing tricyclic aminoalcohol 3 and Baeyer-Villiger oxidation of ketone 8 providing the corresponding lactone 2. Both reactions proceeded regiospecifically.

AB - The efficient synthesis of 3-azabicyclo [3.3.0]octane derivative 1 and a novel tricyclicaminoether 11 has been achieved in seven steps using commercially available starting materials and commonly used reagents. The key steps are the intramolecular ring opening of epoxide 7 providing tricyclic aminoalcohol 3 and Baeyer-Villiger oxidation of ketone 8 providing the corresponding lactone 2. Both reactions proceeded regiospecifically.

KW - Baeyer-Villiger oxidation

KW - Cage-like oxaheterocycle

KW - Intramolecular cyclization

KW - Tricyclicaminoether

UR - http://www.scopus.com/inward/record.url?scp=0242331184&partnerID=8YFLogxK

U2 - 10.1081/SCC-120025195

DO - 10.1081/SCC-120025195

M3 - Article

AN - SCOPUS:0242331184

SN - 0039-7911

VL - 33

SP - 3833

EP - 3841

JO - Synthetic Communications

JF - Synthetic Communications

IS - 21

ER -

Synthesis of 3-Azabicyclo[3.3.0]octane Framework and a Novel Tricyclicaminoether

Abstract

Keywords

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