Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates

Kai Hong; James P. Morken

doi:10.1021/ja402569j

Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates

Kai Hong
, James P. Morken^*

^*Corresponding author for this work

Boston College

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

83 Scopus citations

Abstract

We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B₂(pin)₂ across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl α-amino boronic ester derivatives.

Original language	English
Pages (from-to)	9252-9254
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	135
Issue number	25
DOIs	https://doi.org/10.1021/ja402569j
State	Published - 26 Jun 2013
Externally published	Yes

Access to Document

10.1021/ja402569j

Cite this

@article{d7856f1e54984d66a62dc7f01d57b487,

title = "Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates",

abstract = "We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B2(pin)2 across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl α-amino boronic ester derivatives.",

author = "Kai Hong and Morken, \{James P.\}",

year = "2013",

month = jun,

day = "26",

doi = "10.1021/ja402569j",

language = "英语",

volume = "135",

pages = "9252--9254",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "25",

}

TY - JOUR

T1 - Catalytic enantioselective one-pot aminoborylation of aldehydes

T2 - A strategy for construction of nonracemic α-amino boronates

AU - Hong, Kai

AU - Morken, James P.

PY - 2013/6/26

Y1 - 2013/6/26

N2 - We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B2(pin)2 across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl α-amino boronic ester derivatives.

AB - We report a strategy for the conversion of aldehydes to enantiomerically enriched α-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B2(pin)2 across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl α-amino boronic ester derivatives.

UR - https://www.scopus.com/pages/publications/84879537309

U2 - 10.1021/ja402569j

DO - 10.1021/ja402569j

M3 - 文章

C2 - 23763463

AN - SCOPUS:84879537309

SN - 0002-7863

VL - 135

SP - 9252

EP - 9254

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 25

ER -

Catalytic enantioselective one-pot aminoborylation of aldehydes: A strategy for construction of nonracemic α-amino boronates

Abstract

Access to Document

Other files and links

Fingerprint

Cite this