Enantioselective Synthesis of Dual Serotonergic Azanoradamantane SC-52491

Daniel Becker; Robert K. Husa; Alan E. Moormann; Clara I. Villamil

doi:10.1016/S0040-4020(99)00680-8

Enantioselective Synthesis of Dual Serotonergic Azanoradamantane SC-52491

Daniel Becker
, Robert K. Husa
, Alan E. Moormann
, Clara I. Villamil

Department of Chemistry and Biochemistry

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

Abstract

A racemic synthesis of azanoradamantane (±)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e.

Original language	American English
Journal	Chemistry: Faculty Publications and Other Works
Volume	55
Issue number	40
DOIs	https://doi.org/10.1016/S0040-4020(99)00680-8
State	Published - Oct 1 1999

Keywords

enantioselective synthesis
serotonergic azanoradamantane

Disciplines

Chemistry

Access to Document

10.1016/S0040-4020(99)00680-8License: Unspecified

Enantioselective Synthesis of Dual Serotonergic AzanoradamantaneFinal published version, 216 KBLicense: Unspecified

Cite this

@article{8ed473468a5b4ecfb832e2c320c5fb73,

title = "Enantioselective Synthesis of Dual Serotonergic Azanoradamantane SC-52491",

abstract = " A racemic synthesis of azanoradamantane (±)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3\% e.e.",

keywords = "enantioselective synthesis, serotonergic azanoradamantane",

author = "Daniel Becker and Husa, \{Robert K.\} and Moormann, \{Alan E.\} and Villamil, \{Clara I.\}",

year = "1999",

month = oct,

day = "1",

doi = "10.1016/S0040-4020(99)00680-8",

language = "American English",

volume = "55",

journal = "Chemistry: Faculty Publications and Other Works",

number = "40",

}

TY - JOUR

T1 - Enantioselective Synthesis of Dual Serotonergic Azanoradamantane SC-52491

AU - Becker, Daniel

AU - Husa, Robert K.

AU - Moormann, Alan E.

AU - Villamil, Clara I.

PY - 1999/10/1

Y1 - 1999/10/1

N2 - A racemic synthesis of azanoradamantane (±)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e.

AB - A racemic synthesis of azanoradamantane (±)-3 was accomplished via Yamamoto's MAD-catalyzed Diels-Alder protocol. Subsequently, a scalable asymmetric synthesis of azanoradamantane benzamide SC-52491 was carried out employing Helmchen's asymmetric Diels-Alder methodology to construct all four contiguous asymmetric centers with the correct relative stereochemistry and in 99.3% e.e.

KW - enantioselective synthesis

KW - serotonergic azanoradamantane

UR - https://ecommons.luc.edu/chemistry_facpubs/16

U2 - 10.1016/S0040-4020(99)00680-8

DO - 10.1016/S0040-4020(99)00680-8

M3 - Article

VL - 55

JO - Chemistry: Faculty Publications and Other Works

JF - Chemistry: Faculty Publications and Other Works

IS - 40

ER -

Enantioselective Synthesis of Dual Serotonergic Azanoradamantane SC-52491

Abstract

Keywords

Disciplines

Access to Document

Other files and links

Cite this