Asymmetric Synthesis of Tertiary and Quaternary Allyl- and Crotylsilanes via the Borylation of Lithiated Carbamates

Varinder K. Aggarwal; Michael Binanzer; M. Carolina de Ceglie; Maddalena Gallanti; Ben W Glasspoole; Stephanie J. F. Kendrick; Ravindra P Sonawane; Ana Vazquez-Romero; Matthew P Webster

doi:10.1021/ol200177f

Asymmetric Synthesis of Tertiary and Quaternary Allyl- and Crotylsilanes via the Borylation of Lithiated Carbamates

Varinder K. Aggarwal^*, Michael Binanzer, M. Carolina de Ceglie, Maddalena Gallanti, Ben W Glasspoole, Stephanie J. F. Kendrick, Ravindra P Sonawane, Ana Vazquez-Romero, Matthew P Webster

^*Corresponding author for this work

School of Chemistry

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

75 Citations (Scopus)

Abstract

Tertiary allyl- or crotylsilanes have been prepared in high er and dr via the lithiation-borylation reaction of alkyl carbamates with silaboronates. Using a related strategy, quaternary allylsilanes could be accessed in similarly high er.

Original language	English
Pages (from-to)	1490-1493
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	6
DOIs	https://doi.org/10.1021/ol200177f
Publication status	Published - 18 Mar 2011

Keywords

ENANTIOSELECTIVE SYNTHESIS
STEREOCONTROLLED SYNTHESIS
STEREOSELECTIVE-SYNTHESIS
BORONIC ESTERS
ALLYLSILANES
REAGENTS
DEPROTONATION
SUBSTITUTIONS
SILYLBORANES
CARBENOIDS

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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

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@article{0d87286029654ec78a5f06e1a38f230e,

title = "Asymmetric Synthesis of Tertiary and Quaternary Allyl- and Crotylsilanes via the Borylation of Lithiated Carbamates",

abstract = "Tertiary allyl- or crotylsilanes have been prepared in high er and dr via the lithiation-borylation reaction of alkyl carbamates with silaboronates. Using a related strategy, quaternary allylsilanes could be accessed in similarly high er.",

keywords = "ENANTIOSELECTIVE SYNTHESIS, STEREOCONTROLLED SYNTHESIS, STEREOSELECTIVE-SYNTHESIS, BORONIC ESTERS, ALLYLSILANES, REAGENTS, DEPROTONATION, SUBSTITUTIONS, SILYLBORANES, CARBENOIDS",

author = "Aggarwal, {Varinder K.} and Michael Binanzer and {de Ceglie}, {M. Carolina} and Maddalena Gallanti and Glasspoole, {Ben W} and Kendrick, {Stephanie J. F.} and Sonawane, {Ravindra P} and Ana Vazquez-Romero and Webster, {Matthew P}",

year = "2011",

month = mar,

day = "18",

doi = "10.1021/ol200177f",

language = "English",

volume = "13",

pages = "1490--1493",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "6",

}

TY - JOUR

T1 - Asymmetric Synthesis of Tertiary and Quaternary Allyl- and Crotylsilanes via the Borylation of Lithiated Carbamates

AU - Aggarwal, Varinder K.

AU - Binanzer, Michael

AU - de Ceglie, M. Carolina

AU - Gallanti, Maddalena

AU - Glasspoole, Ben W

AU - Kendrick, Stephanie J. F.

AU - Sonawane, Ravindra P

AU - Vazquez-Romero, Ana

AU - Webster, Matthew P

PY - 2011/3/18

Y1 - 2011/3/18

N2 - Tertiary allyl- or crotylsilanes have been prepared in high er and dr via the lithiation-borylation reaction of alkyl carbamates with silaboronates. Using a related strategy, quaternary allylsilanes could be accessed in similarly high er.

AB - Tertiary allyl- or crotylsilanes have been prepared in high er and dr via the lithiation-borylation reaction of alkyl carbamates with silaboronates. Using a related strategy, quaternary allylsilanes could be accessed in similarly high er.

KW - ENANTIOSELECTIVE SYNTHESIS

KW - STEREOCONTROLLED SYNTHESIS

KW - STEREOSELECTIVE-SYNTHESIS

KW - BORONIC ESTERS

KW - ALLYLSILANES

KW - REAGENTS

KW - DEPROTONATION

KW - SUBSTITUTIONS

KW - SILYLBORANES

KW - CARBENOIDS

U2 - 10.1021/ol200177f

DO - 10.1021/ol200177f

M3 - Article (Academic Journal)

C2 - 21332157

SN - 1523-7060

VL - 13

SP - 1490

EP - 1493

JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Asymmetric Synthesis of Tertiary and Quaternary Allyl- and Crotylsilanes via the Borylation of Lithiated Carbamates

Abstract

Keywords

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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS

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