Gold(I)-Catalyzed Intramolecular Dehydrative Amination of Sulfamate Esters Tethered to Allylic Alcohols: A Strategy for the Synthesis of Cyclic Sulfamidates

Yunjeong Park; Ji Sun Lee; Jae Sang Ryu

doi:10.1002/adsc.202001330

Gold(I)-Catalyzed Intramolecular Dehydrative Amination of Sulfamate Esters Tethered to Allylic Alcohols: A Strategy for the Synthesis of Cyclic Sulfamidates

Yunjeong Park, Ji Sun Lee, Jae Sang Ryu

Department of Pharmaceutical Sciences

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

6 Scopus citations

Abstract

An efficient synthesis protocol for cyclic sulfamidates has been developed via catalytic intramolecular cyclizations of sulfamate esters tethered to allylic alcohols. The reactions proceed smoothly at room temperature in the presence of (IPr)AuCl (5 mol%) and AgBF₄ (5 mol%). This protocol features good to excellent yields, high selectivity, broad substrate scope, and mild reaction conditions. This method is also applicable to the synthesis of a seven-membered sulfamidate. (Figure presented.).

Original language	English
Pages (from-to)	2183-2188
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	363
Issue number	8
DOIs	https://doi.org/10.1002/adsc.202001330
State	Published - 13 Apr 2021

Bibliographical note

Funding Information:
This research was supported by National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (NRF‐2018R1A5A2025286) and (NRF‐2020R1F1A1052496).

Publisher Copyright:
© 2021 Wiley-VCH GmbH

Keywords

Amination
Cyclic sulfamidate
Gold
Homogeneous catalysis
Silver

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title = "Gold(I)-Catalyzed Intramolecular Dehydrative Amination of Sulfamate Esters Tethered to Allylic Alcohols: A Strategy for the Synthesis of Cyclic Sulfamidates",

abstract = "An efficient synthesis protocol for cyclic sulfamidates has been developed via catalytic intramolecular cyclizations of sulfamate esters tethered to allylic alcohols. The reactions proceed smoothly at room temperature in the presence of (IPr)AuCl (5 mol%) and AgBF4 (5 mol%). This protocol features good to excellent yields, high selectivity, broad substrate scope, and mild reaction conditions. This method is also applicable to the synthesis of a seven-membered sulfamidate. (Figure presented.).",

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AU - Ryu, Jae Sang

N1 - Funding Information: This research was supported by National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (NRF‐2018R1A5A2025286) and (NRF‐2020R1F1A1052496). Publisher Copyright: © 2021 Wiley-VCH GmbH

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AB - An efficient synthesis protocol for cyclic sulfamidates has been developed via catalytic intramolecular cyclizations of sulfamate esters tethered to allylic alcohols. The reactions proceed smoothly at room temperature in the presence of (IPr)AuCl (5 mol%) and AgBF4 (5 mol%). This protocol features good to excellent yields, high selectivity, broad substrate scope, and mild reaction conditions. This method is also applicable to the synthesis of a seven-membered sulfamidate. (Figure presented.).

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Gold(I)-Catalyzed Intramolecular Dehydrative Amination of Sulfamate Esters Tethered to Allylic Alcohols: A Strategy for the Synthesis of Cyclic Sulfamidates

Abstract

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Keywords

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