Synthesis of 6- and 7-Membered N-Heterocycles Using α-Phenylvinylsulfonium Salts

Johnathan V. Matlock; Thomas D. Svejstrup; Pradip Songara; Sarah Overington; Eoghan M McGarrigle; Varinder K Aggarwal

doi:10.1021/acs.orglett.5b02516

Synthesis of 6- and 7-Membered N-Heterocycles Using α-Phenylvinylsulfonium Salts

Johnathan V. Matlock
, Thomas D. Svejstrup
, Pradip Songara
, Sarah Overington
, Eoghan M McGarrigle^*
, Varinder K Aggarwal

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

94 Citations (Scopus)

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Abstract

A concise synthesis of stereodefined C-substituted morpholines, piperazines, azepines, and oxazepines in moderate to excellent yields (27% to 75%) is reported by reaction of 1,2- or 1,3-amino alcohol/1,2- or 1,3-diamine with an α-phenylvinylsulfonium salt. High levels of regio- and diastereoselectivity (from 2:1 to >20:1) are observed through judicious choice of base (Cs₂CO₃) and solvent (CH₂Cl₂). Reactions are performed at ambient temperature and open to air and do not require anhydrous solvent. The deprotection of the N-sulfonamide protecting groups (N-Ts and N-Ns) is also demonstrated. Factors affecting regio- and diastereocontrol are discussed.

Original language	English
Pages (from-to)	5044-5047
Number of pages	4
Journal	Organic Letters
Volume	17
Issue number	20
Early online date	30 Sept 2015
DOIs	https://doi.org/10.1021/acs.orglett.5b02516
Publication status	Published - 16 Oct 2015

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Organic & Biological

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10.1021/acs.orglett.5b02516

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This is the author accepted manuscript (AAM). The final published version (version of record) is available online via ACS at http://pubs.acs.org/doi/10.1021/acs.orglett.5b02516. Please refer to any applicable terms of use of the publisher.
Accepted author manuscript, 854 KBLicence: Unspecified

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title = "Synthesis of 6- and 7-Membered N-Heterocycles Using α-Phenylvinylsulfonium Salts",

abstract = "A concise synthesis of stereodefined C-substituted morpholines, piperazines, azepines, and oxazepines in moderate to excellent yields (27\% to 75\%) is reported by reaction of 1,2- or 1,3-amino alcohol/1,2- or 1,3-diamine with an α-phenylvinylsulfonium salt. High levels of regio- and diastereoselectivity (from 2:1 to >20:1) are observed through judicious choice of base (Cs2CO3) and solvent (CH2Cl2). Reactions are performed at ambient temperature and open to air and do not require anhydrous solvent. The deprotection of the N-sulfonamide protecting groups (N-Ts and N-Ns) is also demonstrated. Factors affecting regio- and diastereocontrol are discussed.",

author = "Matlock, \{Johnathan V.\} and Svejstrup, \{Thomas D.\} and Pradip Songara and Sarah Overington and McGarrigle, \{Eoghan M\} and Aggarwal, \{Varinder K\}",

year = "2015",

month = oct,

day = "16",

doi = "10.1021/acs.orglett.5b02516",

language = "English",

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journal = "Organic Letters",

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T1 - Synthesis of 6- and 7-Membered N-Heterocycles Using α-Phenylvinylsulfonium Salts

AU - Matlock, Johnathan V.

AU - Svejstrup, Thomas D.

AU - Songara, Pradip

AU - Overington, Sarah

AU - McGarrigle, Eoghan M

AU - Aggarwal, Varinder K

PY - 2015/10/16

Y1 - 2015/10/16

N2 - A concise synthesis of stereodefined C-substituted morpholines, piperazines, azepines, and oxazepines in moderate to excellent yields (27% to 75%) is reported by reaction of 1,2- or 1,3-amino alcohol/1,2- or 1,3-diamine with an α-phenylvinylsulfonium salt. High levels of regio- and diastereoselectivity (from 2:1 to >20:1) are observed through judicious choice of base (Cs2CO3) and solvent (CH2Cl2). Reactions are performed at ambient temperature and open to air and do not require anhydrous solvent. The deprotection of the N-sulfonamide protecting groups (N-Ts and N-Ns) is also demonstrated. Factors affecting regio- and diastereocontrol are discussed.

AB - A concise synthesis of stereodefined C-substituted morpholines, piperazines, azepines, and oxazepines in moderate to excellent yields (27% to 75%) is reported by reaction of 1,2- or 1,3-amino alcohol/1,2- or 1,3-diamine with an α-phenylvinylsulfonium salt. High levels of regio- and diastereoselectivity (from 2:1 to >20:1) are observed through judicious choice of base (Cs2CO3) and solvent (CH2Cl2). Reactions are performed at ambient temperature and open to air and do not require anhydrous solvent. The deprotection of the N-sulfonamide protecting groups (N-Ts and N-Ns) is also demonstrated. Factors affecting regio- and diastereocontrol are discussed.

UR - https://www.scopus.com/pages/publications/84944937845

U2 - 10.1021/acs.orglett.5b02516

DO - 10.1021/acs.orglett.5b02516

M3 - Article (Academic Journal)

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SN - 1523-7060

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SP - 5044

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JO - Organic Letters

JF - Organic Letters

IS - 20

ER -

Synthesis of 6- and 7-Membered N-Heterocycles Using α-Phenylvinylsulfonium Salts

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Synthesis of 6- and 7-Membered N-Heterocycles Using α-Phenylvinylsulfonium Salts

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