Enantioselective Organocatalyzed Direct α-Thiocyanation of Cyclic β-Ketoesters by N -Thiocyanatophthalimide

Jiashen Qiu; Di Wu; Pran Gopal Karmaker; Hongquan Yin; Fu Xue Chen

doi:10.1021/acs.orglett.8b00342

Enantioselective Organocatalyzed Direct α-Thiocyanation of Cyclic β-Ketoesters by N -Thiocyanatophthalimide

Jiashen Qiu, Di Wu, Pran Gopal Karmaker, Hongquan Yin, Fu Xue Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

75 Citations (Scopus)

Abstract

A new electrophilic thiocyanation reagent, N-thiocyanatophthalimide, was synthesized and applied to the first example of catalytic asymmetric electrophilic α-thiocyanation of various cyclic β-ketoesters by the bifunctional cinchona alkaloid catalysis. Thus, a variety of chiral α-thiocyanato β-ketoesters with a quaternary carbon center have been achieved in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) in a convenient manner.

Original language	English
Pages (from-to)	1600-1603
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	6
DOIs	https://doi.org/10.1021/acs.orglett.8b00342
Publication status	Published - 16 Mar 2018

Access to Document

10.1021/acs.orglett.8b00342

Cite this

@article{a7e91aa15f4c4016b318ea12a988d2f4,

title = "Enantioselective Organocatalyzed Direct α-Thiocyanation of Cyclic β-Ketoesters by N -Thiocyanatophthalimide",

abstract = "A new electrophilic thiocyanation reagent, N-thiocyanatophthalimide, was synthesized and applied to the first example of catalytic asymmetric electrophilic α-thiocyanation of various cyclic β-ketoesters by the bifunctional cinchona alkaloid catalysis. Thus, a variety of chiral α-thiocyanato β-ketoesters with a quaternary carbon center have been achieved in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) in a convenient manner.",

author = "Jiashen Qiu and Di Wu and Karmaker, {Pran Gopal} and Hongquan Yin and Chen, {Fu Xue}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = mar,

day = "16",

doi = "10.1021/acs.orglett.8b00342",

language = "English",

volume = "20",

pages = "1600--1603",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Enantioselective Organocatalyzed Direct α-Thiocyanation of Cyclic β-Ketoesters by N -Thiocyanatophthalimide

AU - Qiu, Jiashen

AU - Wu, Di

AU - Karmaker, Pran Gopal

AU - Yin, Hongquan

AU - Chen, Fu Xue

PY - 2018/3/16

Y1 - 2018/3/16

N2 - A new electrophilic thiocyanation reagent, N-thiocyanatophthalimide, was synthesized and applied to the first example of catalytic asymmetric electrophilic α-thiocyanation of various cyclic β-ketoesters by the bifunctional cinchona alkaloid catalysis. Thus, a variety of chiral α-thiocyanato β-ketoesters with a quaternary carbon center have been achieved in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) in a convenient manner.

AB - A new electrophilic thiocyanation reagent, N-thiocyanatophthalimide, was synthesized and applied to the first example of catalytic asymmetric electrophilic α-thiocyanation of various cyclic β-ketoesters by the bifunctional cinchona alkaloid catalysis. Thus, a variety of chiral α-thiocyanato β-ketoesters with a quaternary carbon center have been achieved in excellent yields (up to 99%) and high enantioselectivities (up to 94% ee) in a convenient manner.

UR - http://www.scopus.com/inward/record.url?scp=85044092591&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.8b00342

DO - 10.1021/acs.orglett.8b00342

M3 - Article

C2 - 29474092

AN - SCOPUS:85044092591

SN - 1523-7060

VL - 20

SP - 1600

EP - 1603

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Enantioselective Organocatalyzed Direct α-Thiocyanation of Cyclic β-Ketoesters by N -Thiocyanatophthalimide

Abstract

Access to Document

Other files and links

Fingerprint

Cite this