Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation-Protodeboronation Methodology

Stefan Roesner; Javier Mansilla Casatejada; Tim G. Elford; Ravindra P. Sonawane; Varinder K. Aggarwal

doi:10.1021/ol202251p

Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation-Protodeboronation Methodology

Stefan Roesner
, Javier Mansilla Casatejada
, Tim G. Elford
, Ravindra P. Sonawane
, Varinder K. Aggarwal^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

95 Citations (Scopus)

Abstract

The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCI, H2O), or a solvent switch to CHCI3, to achieve high yields and high selectivities.

Original language	English
Pages (from-to)	5740-5743
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	21
DOIs	https://doi.org/10.1021/ol202251p
Publication status	Published - 4 Nov 2011

Research Groups and Themes

Organic & Biological

Keywords

TERTIARY BORONIC ESTERS
ASYMMETRIC-SYNTHESIS
ELECTROPHILIC SUBSTITUTION
SECONDARY ALCOHOLS
SERTRALINE
DIASTEREOSELECTIVITY
GENERATION
CONVERSION
REDUCTION
SEROTONIN

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/05 → 1/10/10
Project: Research

Cite this

@article{ef03b0b83c884587acc20d293fb8396a,

title = "Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation-Protodeboronation Methodology",

abstract = "The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCI, H2O), or a solvent switch to CHCI3, to achieve high yields and high selectivities.",

keywords = "TERTIARY BORONIC ESTERS, ASYMMETRIC-SYNTHESIS, ELECTROPHILIC SUBSTITUTION, SECONDARY ALCOHOLS, SERTRALINE, DIASTEREOSELECTIVITY, GENERATION, CONVERSION, REDUCTION, SEROTONIN",

author = "Stefan Roesner and Casatejada, \{Javier Mansilla\} and Elford, \{Tim G.\} and Sonawane, \{Ravindra P.\} and Aggarwal, \{Varinder K.\}",

year = "2011",

month = nov,

day = "4",

doi = "10.1021/ol202251p",

language = "English",

volume = "13",

pages = "5740--5743",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation-Protodeboronation Methodology

AU - Roesner, Stefan

AU - Casatejada, Javier Mansilla

AU - Elford, Tim G.

AU - Sonawane, Ravindra P.

AU - Aggarwal, Varinder K.

PY - 2011/11/4

Y1 - 2011/11/4

N2 - The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCI, H2O), or a solvent switch to CHCI3, to achieve high yields and high selectivities.

AB - The lithiation/borylation-protodeboronation of a homoallyl carbamate was applied to the synthesis of (+)-sertraline and (+)-indatraline. Due to the presence of the alkene, significant modifications of the methodology were required (use of 12-crown-4, TMSCI, H2O), or a solvent switch to CHCI3, to achieve high yields and high selectivities.

KW - TERTIARY BORONIC ESTERS

KW - ASYMMETRIC-SYNTHESIS

KW - ELECTROPHILIC SUBSTITUTION

KW - SECONDARY ALCOHOLS

KW - SERTRALINE

KW - DIASTEREOSELECTIVITY

KW - GENERATION

KW - CONVERSION

KW - REDUCTION

KW - SEROTONIN

U2 - 10.1021/ol202251p

DO - 10.1021/ol202251p

M3 - Article (Academic Journal)

C2 - 21995597

SN - 1523-7060

VL - 13

SP - 5740

EP - 5743

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Enantioselective Syntheses of (+)-Sertraline and (+)-Indatraline Using Lithiation/Borylation-Protodeboronation Methodology

Abstract

Research Groups and Themes

Keywords

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

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