Enantioselective 1,2-Addition of α-Aminoalkyl Radical to Aldehydes via Visible-Light Photoredox Initiated Chiral Oxazaborolidinium Ion Catalysis

Jae Yeon Kim; Yea Suel Lee; Yuna Choi; Do Hyun Ryu

doi:10.1021/acscatal.0c02443

Enantioselective 1,2-Addition of α-Aminoalkyl Radical to Aldehydes via Visible-Light Photoredox Initiated Chiral Oxazaborolidinium Ion Catalysis

Jae Yeon Kim, Yea Suel Lee, Yuna Choi, Do Hyun Ryu

Department of Chemistry

Sungkyunkwan University

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

32 Scopus citations

Abstract

Enantioselective 1,2-Addition reaction of α-Aminoalkyl radical to α,β-unsaturated or aromatic aldehydes to synthesize highly optically active β-Amino alcohols has been developed. In the presence of chiral oxazaborolidinium ion catalyst and photosensitizer, the reaction provides desired β-Amino allylic or benzylic alcohols with high yields (up to 99%) and high enantioselectivities (up to 98% ee).

Original language	English
Pages (from-to)	10585-10591
Number of pages	7
Journal	ACS Catalysis
Volume	10
Issue number	18
DOIs	https://doi.org/10.1021/acscatal.0c02443
State	Published - 18 Sep 2020

Keywords

asymmetric synthesis
Lewis acids
radical 1,2-Addition
α-Aminoalkyl radical
β-Amino alcohol

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10.1021/acscatal.0c02443

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title = "Enantioselective 1,2-Addition of α-Aminoalkyl Radical to Aldehydes via Visible-Light Photoredox Initiated Chiral Oxazaborolidinium Ion Catalysis",

abstract = "Enantioselective 1,2-Addition reaction of α-Aminoalkyl radical to α,β-unsaturated or aromatic aldehydes to synthesize highly optically active β-Amino alcohols has been developed. In the presence of chiral oxazaborolidinium ion catalyst and photosensitizer, the reaction provides desired β-Amino allylic or benzylic alcohols with high yields (up to 99\%) and high enantioselectivities (up to 98\% ee).",

keywords = "asymmetric synthesis, Lewis acids, radical 1,2-Addition, α-Aminoalkyl radical, β-Amino alcohol",

author = "Kim, \{Jae Yeon\} and Lee, \{Yea Suel\} and Yuna Choi and Ryu, \{Do Hyun\}",

note = "Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

year = "2020",

month = sep,

day = "18",

doi = "10.1021/acscatal.0c02443",

language = "English",

volume = "10",

pages = "10585--10591",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

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T1 - Enantioselective 1,2-Addition of α-Aminoalkyl Radical to Aldehydes via Visible-Light Photoredox Initiated Chiral Oxazaborolidinium Ion Catalysis

AU - Kim, Jae Yeon

AU - Lee, Yea Suel

AU - Choi, Yuna

AU - Ryu, Do Hyun

PY - 2020/9/18

Y1 - 2020/9/18

N2 - Enantioselective 1,2-Addition reaction of α-Aminoalkyl radical to α,β-unsaturated or aromatic aldehydes to synthesize highly optically active β-Amino alcohols has been developed. In the presence of chiral oxazaborolidinium ion catalyst and photosensitizer, the reaction provides desired β-Amino allylic or benzylic alcohols with high yields (up to 99%) and high enantioselectivities (up to 98% ee).

AB - Enantioselective 1,2-Addition reaction of α-Aminoalkyl radical to α,β-unsaturated or aromatic aldehydes to synthesize highly optically active β-Amino alcohols has been developed. In the presence of chiral oxazaborolidinium ion catalyst and photosensitizer, the reaction provides desired β-Amino allylic or benzylic alcohols with high yields (up to 99%) and high enantioselectivities (up to 98% ee).

KW - asymmetric synthesis

KW - Lewis acids

KW - radical 1,2-Addition

KW - α-Aminoalkyl radical

KW - β-Amino alcohol

UR - https://www.scopus.com/pages/publications/85095444676

U2 - 10.1021/acscatal.0c02443

DO - 10.1021/acscatal.0c02443

M3 - Article

AN - SCOPUS:85095444676

SN - 2155-5435

VL - 10

SP - 10585

EP - 10591

JO - ACS Catalysis

JF - ACS Catalysis

IS - 18

ER -

Enantioselective 1,2-Addition of α-Aminoalkyl Radical to Aldehydes via Visible-Light Photoredox Initiated Chiral Oxazaborolidinium Ion Catalysis

Abstract

Keywords

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