Enantioselective construction of quaternary α-carbon centers on α-amino phosphonates via catalytic asymmetric allylation

Ryoichi Kuwano; Ryo Nishio; Yoshihiko Ito

doi:10.1021/ol990679f

Enantioselective construction of quaternary α-carbon centers on α-amino phosphonates via catalytic asymmetric allylation

Ryoichi Kuwano, Ryo Nishio, Yoshihiko Ito

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

76 Citations (Scopus)

Abstract

(equation presented) Asymmetric allylation of α-acetamido β-keto phosphonates was promoted, in the presence of potassium tert-butoxide as a base, by a palladium catalyst prepared from [Pd(π-allyl)(cod)]BF₄ and (R)-BINAP and gave the corresponding α-alkyl α-amino phosphonic acid derivatives with 65-88% ee. Diastereoselective reduction of the carbonyl group in the product was accomplished by NaBH₄ or Bu₄NBH₄. The diastereoselection in the reduction was reversed by choice of solvent.

Original language	English
Pages (from-to)	837-839
Number of pages	3
Journal	Organic letters
Volume	1
Issue number	6
DOIs	https://doi.org/10.1021/ol990679f
Publication status	Published - Sept 23 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol990679f

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title = "Enantioselective construction of quaternary α-carbon centers on α-amino phosphonates via catalytic asymmetric allylation",

abstract = "(equation presented) Asymmetric allylation of α-acetamido β-keto phosphonates was promoted, in the presence of potassium tert-butoxide as a base, by a palladium catalyst prepared from [Pd(π-allyl)(cod)]BF4 and (R)-BINAP and gave the corresponding α-alkyl α-amino phosphonic acid derivatives with 65-88% ee. Diastereoselective reduction of the carbonyl group in the product was accomplished by NaBH4 or Bu4NBH4. The diastereoselection in the reduction was reversed by choice of solvent.",

author = "Ryoichi Kuwano and Ryo Nishio and Yoshihiko Ito",

year = "1999",

month = sep,

day = "23",

doi = "10.1021/ol990679f",

language = "English",

volume = "1",

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journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Enantioselective construction of quaternary α-carbon centers on α-amino phosphonates via catalytic asymmetric allylation

AU - Kuwano, Ryoichi

AU - Nishio, Ryo

AU - Ito, Yoshihiko

PY - 1999/9/23

Y1 - 1999/9/23

N2 - (equation presented) Asymmetric allylation of α-acetamido β-keto phosphonates was promoted, in the presence of potassium tert-butoxide as a base, by a palladium catalyst prepared from [Pd(π-allyl)(cod)]BF4 and (R)-BINAP and gave the corresponding α-alkyl α-amino phosphonic acid derivatives with 65-88% ee. Diastereoselective reduction of the carbonyl group in the product was accomplished by NaBH4 or Bu4NBH4. The diastereoselection in the reduction was reversed by choice of solvent.

AB - (equation presented) Asymmetric allylation of α-acetamido β-keto phosphonates was promoted, in the presence of potassium tert-butoxide as a base, by a palladium catalyst prepared from [Pd(π-allyl)(cod)]BF4 and (R)-BINAP and gave the corresponding α-alkyl α-amino phosphonic acid derivatives with 65-88% ee. Diastereoselective reduction of the carbonyl group in the product was accomplished by NaBH4 or Bu4NBH4. The diastereoselection in the reduction was reversed by choice of solvent.

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DO - 10.1021/ol990679f

M3 - Article

AN - SCOPUS:0001687230

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JO - Organic Letters

JF - Organic Letters

IS - 6

ER -

Enantioselective construction of quaternary α-carbon centers on α-amino phosphonates via catalytic asymmetric allylation

Abstract

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