Boron-based pronucleophiles in catalytic (asymmetric) C(sp3)–allyl cross-couplings

Uwe Schneider; Yi-Yong Huang; Ananya Chakrabarti; Hai Thanh Dao; Naohide Morita; Shu̅ Kobayashi

doi:10.1351/PAC-CON-12-05-01

Boron-based pronucleophiles in catalytic (asymmetric) C(sp³)–allyl cross-couplings

Uwe Schneider, Yi-Yong Huang, Ananya Chakrabarti, Hai Thanh Dao, Naohide Morita, Shu̅ Kobayashi

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution

Abstract / Description of output

Allylic and allenyl boronates or boranes were uncovered as suitable pronucleophiles in catalytic C–C bond formations with C(sp³) electrophiles such as O,O-acetals and N,O-aminals or ethers and carbohydrates. These transformations were most efficiently catalyzed by In(I) triflate. Importantly, chiral counteranion-directed, catalytic asymmetric allylation and allenylation of N,O-aminals was developed by employing a catalyst system composed of In(I) chloride and a chiral silver 2,2'-dihydroxy-1,1'-binaphthalene (BINOL)-phosphate.

Original language	English
Title of host publication	Pure and Applied Chemistry
Publisher	International Union of Pure and Applied Chemistry
Pages	2417-2430
Volume	84
Edition	2012
ISBN (Electronic)	1365-3075
ISBN (Print)	0033-4545
DOIs	https://doi.org/10.1351/PAC-CON-12-05-01
Publication status	Published - 28 Aug 2012

Access to Document

10.1351/PAC-CON-12-05-01

Boron-based pronucleophiles in catalytic (asymmetric) C(sp3)–allyl cross-couplings
Copyright © 2012 International Union of Pure and Applied Chemistry. This article may be downloaded for personal use only. Any other use requires prior permission of the author and the IUPAC.
Final published version, 1.73 MB

http://www.iupac.org/publications/pac/84/11/2417/

Cite this

@inproceedings{fea504712eb741b29dcbde076eedab42,

title = "Boron-based pronucleophiles in catalytic (asymmetric) C(sp3)–allyl cross-couplings",

abstract = "Allylic and allenyl boronates or boranes were uncovered as suitable pronucleophiles in catalytic C–C bond formations with C(sp3) electrophiles such as O,O-acetals and N,O-aminals or ethers and carbohydrates. These transformations were most efficiently catalyzed by In(I) triflate. Importantly, chiral counteranion-directed, catalytic asymmetric allylation and allenylation of N,O-aminals was developed by employing a catalyst system composed of In(I) chloride and a chiral silver 2,2'-dihydroxy-1,1'-binaphthalene (BINOL)-phosphate.",

author = "Uwe Schneider and Yi-Yong Huang and Ananya Chakrabarti and Dao, {Hai Thanh} and Naohide Morita and Shu̅ Kobayashi",

year = "2012",

month = aug,

day = "28",

doi = "10.1351/PAC-CON-12-05-01",

language = "English",

isbn = "0033-4545",

volume = "84",

pages = "2417--2430",

booktitle = "Pure and Applied Chemistry",

publisher = "International Union of Pure and Applied Chemistry",

edition = "2012",

}

TY - GEN

T1 - Boron-based pronucleophiles in catalytic (asymmetric) C(sp3)–allyl cross-couplings

AU - Schneider, Uwe

AU - Huang, Yi-Yong

AU - Chakrabarti, Ananya

AU - Dao, Hai Thanh

AU - Morita, Naohide

AU - Kobayashi, Shu̅

PY - 2012/8/28

Y1 - 2012/8/28

N2 - Allylic and allenyl boronates or boranes were uncovered as suitable pronucleophiles in catalytic C–C bond formations with C(sp3) electrophiles such as O,O-acetals and N,O-aminals or ethers and carbohydrates. These transformations were most efficiently catalyzed by In(I) triflate. Importantly, chiral counteranion-directed, catalytic asymmetric allylation and allenylation of N,O-aminals was developed by employing a catalyst system composed of In(I) chloride and a chiral silver 2,2'-dihydroxy-1,1'-binaphthalene (BINOL)-phosphate.

AB - Allylic and allenyl boronates or boranes were uncovered as suitable pronucleophiles in catalytic C–C bond formations with C(sp3) electrophiles such as O,O-acetals and N,O-aminals or ethers and carbohydrates. These transformations were most efficiently catalyzed by In(I) triflate. Importantly, chiral counteranion-directed, catalytic asymmetric allylation and allenylation of N,O-aminals was developed by employing a catalyst system composed of In(I) chloride and a chiral silver 2,2'-dihydroxy-1,1'-binaphthalene (BINOL)-phosphate.

U2 - 10.1351/PAC-CON-12-05-01

DO - 10.1351/PAC-CON-12-05-01

M3 - Conference contribution

SN - 0033-4545

VL - 84

SP - 2417

EP - 2430

BT - Pure and Applied Chemistry

PB - International Union of Pure and Applied Chemistry

ER -

Boron-based pronucleophiles in catalytic (asymmetric) C(sp3)–allyl cross-couplings

Abstract / Description of output

Access to Document

Fingerprint

Cite this

Boron-based pronucleophiles in catalytic (asymmetric) C(sp³)–allyl cross-couplings