Toward a versatile allylation reagent: Practical, enantioselective allylation of acylhydrazones using strained silacycles

被引：102

作者：

Berger, R ^{[1
]}

Rabbat, PMA ^{[1
]}

Leighton, JL ^{[1
]}

机构：

[1] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 32期

关键词：

D O I：

10.1021/ja035001g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly practical method for the enantioselective allylation of acylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of acylhydrazones to give the hydrazide products with good enantioselectivity (83-89% ee, typically). It has been demonstrated that the products may be isolated without chromatography by recrystallization in ≥98% ee. Copyright © 2003 American Chemical Society.

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页码：9596 / 9597

页数：2

相关论文

共 30 条

[1] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[2] Stereochemistry of the allylation and crotylation reactions of α-methyl-β-hydroxy aldehydes with allyl- and crotyltrifluorosilanes.: Synthesis of anti, anti-dipropionate stereotriads and stereodivergent pathways for the reactions with 2,3-anti- and 2,3-syn-α-methyl-β-hydroxy aldehydes [J].

Chemler, SR ;

Roush, WR .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1319-1333

[3] Concerning the synthesis of the elusive anti,anti-dipropionate stereotriad via the crotylation of β-hydroxy α-methyl aldehydes with (Z)-crotyltrifluorosilane.: Application to the synthesis of the C(7)-C(16) segment of zincophorin [J].

Chemler, SR ;

Roush, WR .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (12) :3800-3801

[4]

Chen GM, 1999, ANGEW CHEM INT EDIT, V38, P825, DOI 10.1002/(SICI)1521-3773(19990315)38:6<825::AID-ANIE825>3.0.CO

[5]

2-V

[6] Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond [J].

Enders, D ;

Reinhold, U .

TETRAHEDRON-ASYMMETRY, 1997, 8 (12) :1895-1946

[7] Catalytic approach for the formation of optically active allyl α-amino acids by addition of allylic metal compounds to α-imino esters [J].

Fang, XM ;

Johannsen, M ;

Yao, SL ;

Gathergood, N ;

Hazell, RG ;

Jorgensen, KA .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4844-4849

[8]

Gastner T, 2001, ANGEW CHEM INT EDIT, V40, P1896, DOI 10.1002/1521-3773(20010518)40:10<1896::AID-ANIE1896>3.3.CO

[9]

2-N

[10] Highly stereoselective synthesis of homoallylic amines based on addition of allyltrichlorosilanes to benzoylhydrazones [J].

Hirabayashi, R ;

Ogawa, C ;

Sugiura, M ;

Kobayashi, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (39) :9493-9499