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

Jiashen Qiu; Di Wu; Pran Gopal Karmaker; Hongquan Yin; Fuxue 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
, Fuxue Chen^*

^*Corresponding author for this work

School of Chemistry and Chemical Engineering

Beijing Institute of Technology

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

81 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

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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 Fuxue Chen",

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

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

language = "English",

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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, Fuxue

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 - https://www.scopus.com/pages/publications/85044092591

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

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