Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via Type II Anion Relay Chemistry

Amos B. Smith; Heeoon Han; Won Suk Kim

doi:10.1021/ol2010598

Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via Type II Anion Relay Chemistry

Amos B. Smith, Heeoon Han, Won Suk Kim

Department of Chemistry & Nanoscience

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

37 Scopus citations

Abstract

An effective, general protocol for the Diversity-Oriented Synthesis (DOS) of 2,4,6-trisubstituted piperidine congeners has been designed and validated. The successful strategy entails a modular approach to all possible stereoisomers of the selected piperidine scaffold, exploiting Type II Anion Relay Chemistry (ARC), followed in turn by intramolecular S_N2 cyclization, chemoselective removal of the dithiane moieties and carbonyl reductions.

Original language	English
Pages (from-to)	3328-3331
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	13
DOIs	https://doi.org/10.1021/ol2010598
State	Published - 1 Jul 2011

Access to Document

10.1021/ol2010598

Cite this

@article{6de9c22706694dd5b079e60d8a35fe03,

title = "Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via Type II Anion Relay Chemistry",

abstract = "An effective, general protocol for the Diversity-Oriented Synthesis (DOS) of 2,4,6-trisubstituted piperidine congeners has been designed and validated. The successful strategy entails a modular approach to all possible stereoisomers of the selected piperidine scaffold, exploiting Type II Anion Relay Chemistry (ARC), followed in turn by intramolecular SN2 cyclization, chemoselective removal of the dithiane moieties and carbonyl reductions.",

author = "Smith, {Amos B.} and Heeoon Han and Kim, {Won Suk}",

year = "2011",

month = jul,

day = "1",

doi = "10.1021/ol2010598",

language = "English",

volume = "13",

pages = "3328--3331",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "13",

}

TY - JOUR

T1 - Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via Type II Anion Relay Chemistry

AU - Smith, Amos B.

AU - Han, Heeoon

AU - Kim, Won Suk

PY - 2011/7/1

Y1 - 2011/7/1

N2 - An effective, general protocol for the Diversity-Oriented Synthesis (DOS) of 2,4,6-trisubstituted piperidine congeners has been designed and validated. The successful strategy entails a modular approach to all possible stereoisomers of the selected piperidine scaffold, exploiting Type II Anion Relay Chemistry (ARC), followed in turn by intramolecular SN2 cyclization, chemoselective removal of the dithiane moieties and carbonyl reductions.

AB - An effective, general protocol for the Diversity-Oriented Synthesis (DOS) of 2,4,6-trisubstituted piperidine congeners has been designed and validated. The successful strategy entails a modular approach to all possible stereoisomers of the selected piperidine scaffold, exploiting Type II Anion Relay Chemistry (ARC), followed in turn by intramolecular SN2 cyclization, chemoselective removal of the dithiane moieties and carbonyl reductions.

UR - http://www.scopus.com/inward/record.url?scp=79959694851&partnerID=8YFLogxK

U2 - 10.1021/ol2010598

DO - 10.1021/ol2010598

M3 - Article

C2 - 21644563

AN - SCOPUS:79959694851

SN - 1523-7060

VL - 13

SP - 3328

EP - 3331

JO - Organic Letters

JF - Organic Letters

IS - 13

ER -

Diversity-oriented synthesis of 2,4,6-trisubstituted piperidines via Type II Anion Relay Chemistry

Abstract

Access to Document

Fingerprint

Cite this