Zn-catalyzed asymmetric allylation for the synthesis of optically active allylglycine derivatives. Regio- and stereoselective formal alpha-addition of allylboronates to hydrazono esters

Mari Fujita; Takashi Nagano; Uwe Schneider; Tomoaki Hamada; Chikako Ogawa; Shu Kobayashi

doi:10.1021/ja710627x

Zn-catalyzed asymmetric allylation for the synthesis of optically active allylglycine derivatives. Regio- and stereoselective formal alpha-addition of allylboronates to hydrazono esters

Mari Fujita, Takashi Nagano, Uwe Schneider, Tomoaki Hamada, Chikako Ogawa, Shu Kobayashi

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

Abstract / Description of output

We have developed Zn-catalyzed asymmetric allylation of hydrazono esters with allylboronates. The reactions proceeded smoothly in high yields and high stereoselectivities. Remarkably, formal alpha-addition occurred for alpha-substituted allylboronates exclusively, and excellent stereoselectivities were observed. This is the first example of catalytic regio- and stereoselective allylations with formal alpha-addition. In addition, the reaction proceeded in aqueous media, and the use of water is essential. Zn(OH)(2) might be a catalyst in this asymmetric allylation, and the catalytic activity of Zn(OH)(2) was confirmed. This is also the first case of chiral metal hydroxide-catalyzed asymmetric reactions.

Original language	English
Pages (from-to)	2914-2915
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	130
Issue number	10
DOIs	https://doi.org/10.1021/ja710627x
Publication status	Published - 12 Mar 2008

Access to Document

10.1021/ja710627x

Cite this

@article{1d31e76b6b844150aaacf5eec21e8eb2,

title = "Zn-catalyzed asymmetric allylation for the synthesis of optically active allylglycine derivatives. Regio- and stereoselective formal alpha-addition of allylboronates to hydrazono esters",

abstract = "We have developed Zn-catalyzed asymmetric allylation of hydrazono esters with allylboronates. The reactions proceeded smoothly in high yields and high stereoselectivities. Remarkably, formal alpha-addition occurred for alpha-substituted allylboronates exclusively, and excellent stereoselectivities were observed. This is the first example of catalytic regio- and stereoselective allylations with formal alpha-addition. In addition, the reaction proceeded in aqueous media, and the use of water is essential. Zn(OH)(2) might be a catalyst in this asymmetric allylation, and the catalytic activity of Zn(OH)(2) was confirmed. This is also the first case of chiral metal hydroxide-catalyzed asymmetric reactions.",

author = "Mari Fujita and Takashi Nagano and Uwe Schneider and Tomoaki Hamada and Chikako Ogawa and Shu Kobayashi",

year = "2008",

month = mar,

day = "12",

doi = "10.1021/ja710627x",

language = "English",

volume = "130",

pages = "2914--2915",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "10",

}

Fujita, M, Nagano, T, Schneider, U, Hamada, T, Ogawa, C & Kobayashi, S 2008, 'Zn-catalyzed asymmetric allylation for the synthesis of optically active allylglycine derivatives. Regio- and stereoselective formal alpha-addition of allylboronates to hydrazono esters', Journal of the American Chemical Society, vol. 130, no. 10, pp. 2914-2915. https://doi.org/10.1021/ja710627x

Zn-catalyzed asymmetric allylation for the synthesis of optically active allylglycine derivatives. Regio- and stereoselective formal alpha-addition of allylboronates to hydrazono esters. / Fujita, Mari; Nagano, Takashi; Schneider, Uwe et al.
In: Journal of the American Chemical Society, Vol. 130, No. 10, 12.03.2008, p. 2914-2915.

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

TY - JOUR

T1 - Zn-catalyzed asymmetric allylation for the synthesis of optically active allylglycine derivatives. Regio- and stereoselective formal alpha-addition of allylboronates to hydrazono esters

AU - Fujita, Mari

AU - Nagano, Takashi

AU - Schneider, Uwe

AU - Hamada, Tomoaki

AU - Ogawa, Chikako

AU - Kobayashi, Shu

PY - 2008/3/12

Y1 - 2008/3/12

N2 - We have developed Zn-catalyzed asymmetric allylation of hydrazono esters with allylboronates. The reactions proceeded smoothly in high yields and high stereoselectivities. Remarkably, formal alpha-addition occurred for alpha-substituted allylboronates exclusively, and excellent stereoselectivities were observed. This is the first example of catalytic regio- and stereoselective allylations with formal alpha-addition. In addition, the reaction proceeded in aqueous media, and the use of water is essential. Zn(OH)(2) might be a catalyst in this asymmetric allylation, and the catalytic activity of Zn(OH)(2) was confirmed. This is also the first case of chiral metal hydroxide-catalyzed asymmetric reactions.

AB - We have developed Zn-catalyzed asymmetric allylation of hydrazono esters with allylboronates. The reactions proceeded smoothly in high yields and high stereoselectivities. Remarkably, formal alpha-addition occurred for alpha-substituted allylboronates exclusively, and excellent stereoselectivities were observed. This is the first example of catalytic regio- and stereoselective allylations with formal alpha-addition. In addition, the reaction proceeded in aqueous media, and the use of water is essential. Zn(OH)(2) might be a catalyst in this asymmetric allylation, and the catalytic activity of Zn(OH)(2) was confirmed. This is also the first case of chiral metal hydroxide-catalyzed asymmetric reactions.

U2 - 10.1021/ja710627x

DO - 10.1021/ja710627x

M3 - Article

SN - 0002-7863

VL - 130

SP - 2914

EP - 2915

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 10

ER -

Zn-catalyzed asymmetric allylation for the synthesis of optically active allylglycine derivatives. Regio- and stereoselective formal alpha-addition of allylboronates to hydrazono esters

Abstract / Description of output

Access to Document

Fingerprint

Cite this