Re-enter the syn -(Me,I)Bimane: A Gateway to Bimane Derivatives with Extended π-Systems

Oleg Szumski; Joy Karmakar; Flavio Grynszpan

doi:10.1055/s-0040-1706045

Re-enter the syn -(Me,I)Bimane: A Gateway to Bimane Derivatives with Extended π-Systems

Oleg Szumski, Joy Karmakar, Flavio Grynszpan

Department of Chemical Sciences

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

6 Scopus citations

Abstract

syn -α-Diiodobimane (syn -(R 2,I)B) is a key intermediate for the derivatization of the bimane core in the α-positions. Here we describe an expeditious method to prepare symmetric α-bimane derivatives, such as syn -(R 2,I)B, as well as unsymmetric ones. Our strategy turns the synthesis of α derivatives with extended π-systems practical and affordable. We applied this approach to the synthesis of ethynylbenzaldehyde bearing bimanes as potential selective probes for aldolase class I enzymes.

Original language	English
Pages (from-to)	1141-1145
Number of pages	5
Journal	Synlett
Volume	32
Issue number	11
DOIs	https://doi.org/10.1055/s-0040-1706045
State	Published - 1 Jul 2021

Keywords

bimane
derivatives
fluorescence
intermediate
iodobimane

Access to Document

10.1055/s-0040-1706045

Cite this

@article{88adcdb9ca564a8199fa9d6cc0e76da6,

title = "Re-enter the syn -(Me,I)Bimane: A Gateway to Bimane Derivatives with Extended π-Systems",

abstract = "syn -α-Diiodobimane (syn -(R 2,I)B) is a key intermediate for the derivatization of the bimane core in the α-positions. Here we describe an expeditious method to prepare symmetric α-bimane derivatives, such as syn -(R 2,I)B, as well as unsymmetric ones. Our strategy turns the synthesis of α derivatives with extended π-systems practical and affordable. We applied this approach to the synthesis of ethynylbenzaldehyde bearing bimanes as potential selective probes for aldolase class I enzymes.",

keywords = "bimane, derivatives, fluorescence, intermediate, iodobimane",

author = "Oleg Szumski and Joy Karmakar and Flavio Grynszpan",

year = "2021",

month = jul,

day = "1",

doi = "10.1055/s-0040-1706045",

language = "אנגלית",

volume = "32",

pages = "1141--1145",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "11",

}

TY - JOUR

T1 - Re-enter the syn -(Me,I)Bimane

T2 - A Gateway to Bimane Derivatives with Extended π-Systems

AU - Szumski, Oleg

AU - Karmakar, Joy

AU - Grynszpan, Flavio

PY - 2021/7/1

Y1 - 2021/7/1

N2 - syn -α-Diiodobimane (syn -(R 2,I)B) is a key intermediate for the derivatization of the bimane core in the α-positions. Here we describe an expeditious method to prepare symmetric α-bimane derivatives, such as syn -(R 2,I)B, as well as unsymmetric ones. Our strategy turns the synthesis of α derivatives with extended π-systems practical and affordable. We applied this approach to the synthesis of ethynylbenzaldehyde bearing bimanes as potential selective probes for aldolase class I enzymes.

AB - syn -α-Diiodobimane (syn -(R 2,I)B) is a key intermediate for the derivatization of the bimane core in the α-positions. Here we describe an expeditious method to prepare symmetric α-bimane derivatives, such as syn -(R 2,I)B, as well as unsymmetric ones. Our strategy turns the synthesis of α derivatives with extended π-systems practical and affordable. We applied this approach to the synthesis of ethynylbenzaldehyde bearing bimanes as potential selective probes for aldolase class I enzymes.

KW - bimane

KW - derivatives

KW - fluorescence

KW - intermediate

KW - iodobimane

UR - http://www.scopus.com/inward/record.url?scp=85107318419&partnerID=8YFLogxK

U2 - 10.1055/s-0040-1706045

DO - 10.1055/s-0040-1706045

M3 - ???researchoutput.researchoutputtypes.contributiontojournal.article???

AN - SCOPUS:85107318419

SN - 0936-5214

VL - 32

SP - 1141

EP - 1145

JO - Synlett

JF - Synlett

IS - 11

ER -

Re-enter the syn -(Me,I)Bimane: A Gateway to Bimane Derivatives with Extended π-Systems

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this