A novel class of tunable zinc reagents (RXZnCH2Y) for efficient cyclopropanation of olefins

被引：132

作者：

Lorenz, JC ^{[1
]}

Long, J ^{[1
]}

Yang, ZQ ^{[1
]}

Xue, S ^{[1
]}

Xie, Y ^{[1
]}

Shi, Y ^{[1
]}

机构：

[1] Colorado State Univ, Dept Chem, Ft Collins, CO 80523 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 02期

关键词：

D O I：

10.1021/jo030312v

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A class of zinc reagents (RXZnCH2Y) generated with an appropriate organozinc is very effective for the cyclopropanation of olefins. The reactivity and selectivity of these reagents can be regulated by tuning the electronic and steric nature of the RX group on Zn. A reasonable level of enantioselectivity was obtained for the cyclopropanation of unfunctionalized olefins when a chiral (iodomethyl)zinc species was used, providing a valuable approach for the asymmetric cyclopropanation of unfunctionalized olefins.

引用

页码：327 / 334

页数：8

共 127 条

[1] AN ASYMMETRIC SIMMONS-SMITH REACTION
ARAI, I
MORI, A
YAMAMOTO, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (26) : 8254 - 8256
[2] NUCLEOPHILIC STEP OF RING-OPENING REACTIONS OF CYCLOPROPANES WITH ELECTROPHILES - MECHANISM AND STEREOCHEMISTRY .1. REACTION OF 1-PHENYLBICYCLO[4.1.0]HEPTANE WITH MERCURIC-SALTS
BALSAMO, A
BATTISTINI, C
CROTTI, P
MACCHIA, B
MACCHIA, F
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (22) : 3233 - 3237
[3] Asymmetric cyclopropanation of allylic alcohols employing sulfonamide/Schiff base ligands
Balsells, J
Walsh, PJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) : 5005 - 5008
[4] A DFT study of the Simmons-Smith cyclopropanation reaction
Bernardi, F
Bottoni, A
Miscione, GP
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12300 - 12305
[5] CYCLOPROPANE SYNTHESIS FROM METHYLENE IODIDE ZINC-COPPER COUPLE + OLEFINS .2. NATURE OF INTERMEDIATE
BLANCHARD, EP
SIMMONS, HE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (07) : 1337 - &
[6] Magnesium promoted cyclopropanation reactions of allylic alcohols
Bolm, C
Pupowicz, D
[J]. TETRAHEDRON LETTERS, 1997, 38 (42) : 7349 - 7352
[7] Synthesis of the racemic forms of carbon-carbon double bond locked analogues of strobilurins which are characterized by a 2-arylcyclopropane ring cis-substituted at C-1 by the methyl (E)-3-methoxypropenoate unit
Carpita, A
Ribecai, A
Rossi, R
Stabile, P
[J]. TETRAHEDRON, 2002, 58 (19) : 3673 - 3680
[8] Chemical evidence for thiyl radical addition to the C6-position of pyrimidine nucleoside and its possible relevance to DNA damage amplification
Carter, KN
Taverner, T
Schiesser, CH
Greenberg, MM
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) : 8375 - 8378
[9] REACTIONS OF (CO)5WCHC6H5 WITH ALKENES
CASEY, CP
POLICHNOWSKI, SW
SHUSTERMAN, AJ
JONES, CR
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (24) : 7282 - 7292
[10] Charette A.B., 2001, ORG REACT, V58, P1, DOI DOI 10.1002/0471264180.OR058.01

← 1 2 3 4 5 6 7 8 9 10 →