Diastereoselective Simmons-Smith cyclopropanations of allylic amines and carbamates

被引：27

作者：

Davies, Stephen G. ^{[1
]}

Ling, Kenneth B. ^{[1
]}

Roberts, Paul M. ^{[1
]}

Russell, Angela J. ^{[1
]}

Thomson, James E. ^{[1
]}

机构：

[1] Univ Oxford, Dept Organ Chem, Chem Res Lab, Oxford OX1 3TA, England

来源：

CHEMICAL COMMUNICATIONS | 2007年 / 39期

关键词：

D O I：

10.1039/b711358g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclopropanation of 3-(N,N-dibenzylamino) cyclohexene with either Zn(CH2I)(2) ( Wittig-Furukawa reagent) or CF3CO2ZnCH2I (Shi's reagent) gives the corresponding syn-cyclopropane as a single diastereoisomer, whilst cyclopropanation of 3-(N-tert-butoxycarbonylamino) cyclohexene with CF3CO2ZnCH2I gives the corresponding anti-cyclopropane exclusively; facile N-deprotection gives access to either diastereoisomer of the trifluoroacetic acid salt of 2-aminobicyclo[4.1.0] heptane.

引用

页码：4029 / 4031

页数：3

共 31 条

[11] MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES [J].

HENRY, JR ;

MARCIN, LR ;

MCINTOSH, MC ;

SCOLA, PM ;

HARRIS, GD ;

WEINREB, SM .

TETRAHEDRON LETTERS, 1989, 30 (42) :5709-5712

[12] ASYMMETRIC CYCLOPROPANATION OF 1-ALKENYLBORONIC ESTERS AND ITS APPLICATION TO THE SYNTHESIS OF OPTICALLY-ACTIVE CYCLOPROPANOLS [J].

IMAI, T ;

MINETA, H ;

NISHIDA, S .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (17) :4986-4988

[13] Trifluoromethylated amino alcohol as chiral auxiliary for highly diastereoselective and fast Simmons-Smith cyclopropanation of allylic amine [J].

Katagiri, Toshimasa ;

Iguchi, Naomi ;

Kawate, Tomomi ;

Takahashi, Satoshi ;

Uneyama, Kenji .

TETRAHEDRON-ASYMMETRY, 2006, 17 (08) :1157-1160

[14] Diastereoselective cyclopropanation of α,β-unsaturated acetals of a novel camphor-derived chiral auxiliary [J].

Kaye, PT ;

Molema, WE .

CHEMICAL COMMUNICATIONS, 1998, (22) :2479-2480

[15] Stereoselective cyclopropanation reactions [J].

Lebel, H ;

Marcoux, JF ;

Molinaro, C ;

Charette, AB .

CHEMICAL REVIEWS, 2003, 103 (04) :977-1050

[16] A novel class of tunable zinc reagents (RXZnCH2Y) for efficient cyclopropanation of olefins [J].

Lorenz, JC ;

Long, J ;

Yang, ZQ ;

Xue, S ;

Xie, Y ;

Shi, Y .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (02) :327-334

[17]

MARSH EA, 1990, J ORG CHEM, V55, P2045

[18]

MOHAPATRA DK, 2003, J CHEM SOC P1, P1851

[19] SYNTHESIS OF OPTICALLY-ACTIVE CIS- AND TRANS-1,2-DISUBSTITUTED CYCLOPROPANE DERIVATIVES BY THE SIMMONS-SMITH REACTION OF ALLYL ALCOHOL DERIVATIVES DERIVED FROM (R)-2,3-O-ISOPROPYLIDENEGLYCERALDEHYDE [J].

MORIKAWA, T ;

SASAKI, H ;

HANAI, R ;

SHIBUYA, A ;

TAGUCHI, T .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (01) :97-103

[20] A CONCISE ASYMMETRIC-SYNTHESIS OF (-)-ANATOXIN-A USING AN ENANTIOSELECTIVE ENOLIZATION STRATEGY [J].

NEWCOMBE, NJ ;

SIMPKINS, NS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1995, (08) :831-832

← 1 2 3 4 →