Catalytic asymmetric hydrophosphonylation of ketimines

Liang Yin; Youmei Bao; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/ja4059316

Catalytic asymmetric hydrophosphonylation of ketimines

Liang Yin, Youmei Bao, Naoya Kumagai, Masakatsu Shibasaki

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

49 Citations (Scopus)

Abstract

Catalytic asymmetric hydrophosphonylation of aromatic and aliphatic N-thiophosphinoyl ketimines with dialkyl phosphite was efficiently promoted by as little as 0.5 mol% of catalyst loading at ambient temperature. The catalyst can be recovered for repeated use, and facile removal of the thiophosphinoyl group allowed for ready access to the phosphonic acid analogue of enantioenriched α,α-disubstituted α-amino acids.

Original language	English
Pages (from-to)	10338-10341
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	135
Issue number	28
DOIs	https://doi.org/10.1021/ja4059316
Publication status	Published - 2013 Jul 17
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Access to Document

10.1021/ja4059316

Cite this

@article{6b299ff469f54129adf3879b1ee1e223,

title = "Catalytic asymmetric hydrophosphonylation of ketimines",

abstract = "Catalytic asymmetric hydrophosphonylation of aromatic and aliphatic N-thiophosphinoyl ketimines with dialkyl phosphite was efficiently promoted by as little as 0.5 mol% of catalyst loading at ambient temperature. The catalyst can be recovered for repeated use, and facile removal of the thiophosphinoyl group allowed for ready access to the phosphonic acid analogue of enantioenriched α,α-disubstituted α-amino acids.",

author = "Liang Yin and Youmei Bao and Naoya Kumagai and Masakatsu Shibasaki",

year = "2013",

month = jul,

day = "17",

doi = "10.1021/ja4059316",

language = "English",

volume = "135",

pages = "10338--10341",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "28",

}

TY - JOUR

T1 - Catalytic asymmetric hydrophosphonylation of ketimines

AU - Yin, Liang

AU - Bao, Youmei

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2013/7/17

Y1 - 2013/7/17

N2 - Catalytic asymmetric hydrophosphonylation of aromatic and aliphatic N-thiophosphinoyl ketimines with dialkyl phosphite was efficiently promoted by as little as 0.5 mol% of catalyst loading at ambient temperature. The catalyst can be recovered for repeated use, and facile removal of the thiophosphinoyl group allowed for ready access to the phosphonic acid analogue of enantioenriched α,α-disubstituted α-amino acids.

AB - Catalytic asymmetric hydrophosphonylation of aromatic and aliphatic N-thiophosphinoyl ketimines with dialkyl phosphite was efficiently promoted by as little as 0.5 mol% of catalyst loading at ambient temperature. The catalyst can be recovered for repeated use, and facile removal of the thiophosphinoyl group allowed for ready access to the phosphonic acid analogue of enantioenriched α,α-disubstituted α-amino acids.

UR - http://www.scopus.com/inward/record.url?scp=84880350474&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84880350474&partnerID=8YFLogxK

U2 - 10.1021/ja4059316

DO - 10.1021/ja4059316

M3 - Article

C2 - 23819732

AN - SCOPUS:84880350474

SN - 0002-7863

VL - 135

SP - 10338

EP - 10341

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 28

ER -

Catalytic asymmetric hydrophosphonylation of ketimines

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this