1,3-Rearrangement of ketene-N,O-acetals

Tatsuo Suzuki; Masaharu Inui; Seijiro Hosokawa; Susumu Kobayashi

doi:10.1016/S0040-4039(03)00610-5

1,3-Rearrangement of ketene-N,O-acetals

Tatsuo Suzuki, Masaharu Inui, Seijiro Hosokawa, Susumu Kobayashi^*

^*Corresponding author for this work

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

16 Citations (Scopus)

Abstract

Ketene N,O-acetals were prepared stereoselectively and submitted to a Lewis acid-mediated 1,3-rearrangement to afford C-alkylated products. The reactions proceeded in a stereoselective manner to construct a chiral quaternary carbon in high selectivity. The stereochemistry of the quaternary center was found to be opposite to that obtained by an anionic direct dienolate alkylation.

Original language	English
Pages (from-to)	3713-3716
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	18
DOIs	https://doi.org/10.1016/S0040-4039(03)00610-5
Publication status	Published - 2003 Apr 28
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "1,3-Rearrangement of ketene-N,O-acetals",

abstract = "Ketene N,O-acetals were prepared stereoselectively and submitted to a Lewis acid-mediated 1,3-rearrangement to afford C-alkylated products. The reactions proceeded in a stereoselective manner to construct a chiral quaternary carbon in high selectivity. The stereochemistry of the quaternary center was found to be opposite to that obtained by an anionic direct dienolate alkylation.",

author = "Tatsuo Suzuki and Masaharu Inui and Seijiro Hosokawa and Susumu Kobayashi",

note = "Funding Information: This work was supported in part by the Fujisawa Foundation (S.H.) and Grant-in-Aids for Scientific Research from the Ministry of Education, Culture, Sports, and, Science and Technology, Japan.",

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doi = "10.1016/S0040-4039(03)00610-5",

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T1 - 1,3-Rearrangement of ketene-N,O-acetals

AU - Suzuki, Tatsuo

AU - Inui, Masaharu

AU - Hosokawa, Seijiro

AU - Kobayashi, Susumu

N1 - Funding Information: This work was supported in part by the Fujisawa Foundation (S.H.) and Grant-in-Aids for Scientific Research from the Ministry of Education, Culture, Sports, and, Science and Technology, Japan.

PY - 2003/4/28

Y1 - 2003/4/28

N2 - Ketene N,O-acetals were prepared stereoselectively and submitted to a Lewis acid-mediated 1,3-rearrangement to afford C-alkylated products. The reactions proceeded in a stereoselective manner to construct a chiral quaternary carbon in high selectivity. The stereochemistry of the quaternary center was found to be opposite to that obtained by an anionic direct dienolate alkylation.

AB - Ketene N,O-acetals were prepared stereoselectively and submitted to a Lewis acid-mediated 1,3-rearrangement to afford C-alkylated products. The reactions proceeded in a stereoselective manner to construct a chiral quaternary carbon in high selectivity. The stereochemistry of the quaternary center was found to be opposite to that obtained by an anionic direct dienolate alkylation.

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U2 - 10.1016/S0040-4039(03)00610-5

DO - 10.1016/S0040-4039(03)00610-5

M3 - Article

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VL - 44

SP - 3713

EP - 3716

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

1,3-Rearrangement of ketene-N,O-acetals

Abstract

ASJC Scopus subject areas

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