Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

Teemu Yrjö Manuel Niemi; Israel Fernández; Bethany Steadman; Jere Kristian Mannisto; Timo Juhani Repo

doi:10.1039/C8CC00636A

Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

Teemu Yrjö Manuel Niemi, Israel Fernández, Bethany Steadman, Jere Kristian Mannisto, Timo Juhani Repo

Department of Chemistry

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

Abstract

We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.

Original language	English
Journal	Chemical Communications
Volume	54
Issue number	25
Pages (from-to)	3166-3169
Number of pages	4
ISSN	1359-7345
DOIs	https://doi.org/10.1039/C8CC00636A
Publication status	Published - 28 Mar 2018
MoE publication type	A1 Journal article-refereed

Fields of Science

116 Chemical sciences
ATMOSPHERIC-PRESSURE
CARBOXYLATIVE CYCLIZATION
CO2
2-OXAZOLIDINONES
URETHANES
CONVERSION
FIXATION
OXAZOLIDIN-2-ONES
ORGANOCATALYST
AZIRIDINES

Access to Document

10.1039/C8CC00636ALicence: CC BY-NC

c8cc00636aFinal published version, 1.63 MBLicence: CC BY-NC

Cite this

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title = "Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols",

abstract = "We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.",

keywords = "116 Chemical sciences, ATMOSPHERIC-PRESSURE, CARBOXYLATIVE CYCLIZATION, CO2, 2-OXAZOLIDINONES, URETHANES, CONVERSION, FIXATION, OXAZOLIDIN-2-ONES, ORGANOCATALYST, AZIRIDINES",

author = "Niemi, {Teemu Yrj{\"o} Manuel} and Israel Fern{\'a}ndez and Bethany Steadman and Mannisto, {Jere Kristian} and Repo, {Timo Juhani}",

year = "2018",

month = mar,

day = "28",

doi = "10.1039/C8CC00636A",

language = "English",

volume = "54",

pages = "3166--3169",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Carbon dioxide-based facile synthesis of cyclic carbamates from amino alcohols

AU - Niemi, Teemu Yrjö Manuel

AU - Fernández, Israel

AU - Steadman, Bethany

AU - Mannisto, Jere Kristian

AU - Repo, Timo Juhani

PY - 2018/3/28

Y1 - 2018/3/28

N2 - We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.

AB - We report herein a straightforward general method for the synthesis of cyclic carbamates from amino alcohols and carbon dioxide in the presence of an external base and a hydroxyl group activating reagent. Utilizing p-toluenesulfonyl chloride (TsCl), the reaction proceeds under mild conditions, and the approach is fully applicable to the preparation of various high value-added 5- and 6-membered rings as well as bicyclic fused ring carbamates. DFT calculations and experimental results indicate a SN2-type reaction mechanism with high regio-, chemo-, and stereoselectivity.

KW - 116 Chemical sciences

KW - ATMOSPHERIC-PRESSURE

KW - CARBOXYLATIVE CYCLIZATION

KW - CO2

KW - 2-OXAZOLIDINONES

KW - URETHANES

KW - CONVERSION

KW - FIXATION

KW - OXAZOLIDIN-2-ONES

KW - ORGANOCATALYST

KW - AZIRIDINES

U2 - 10.1039/C8CC00636A

DO - 10.1039/C8CC00636A

M3 - Article

VL - 54

SP - 3166

EP - 3169

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 25

ER -