Highly stereoselective addition of organometallic reagents to N-tert-butanesulfinyl imines derived from 3-and 4-substituted cyclohexanones

被引：41

作者：

McMahon, JP ^{[1
]}

Ellman, JA ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Ctr New Direct Organ Synth, Berkeley, CA 94720 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 10期

关键词：

D O I：

10.1021/ol0495220

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of alkyl or aryl Grignard reagents to N-sulfinyl imines derived from 3- and 4-substituted cyclohexanones proceeds with good yields and with excellent diasteroselectivity. The selectivity of the reaction is controlled by the ring substituent rather than the sulfinyl group stereochemistry, and therefore racemic tert-butanesulfinamide can be employed.

引用

页码：1645 / 1647

页数：3

共 10 条

[1] SYNTHESIS OF 3-SUBSTITUTED AND 4-SUBSTITUTED CYCLIC ALPHA-AMINO-ACIDS STRUCTURALLY RELATED TO ACPD
ALONSO, F
MICO, I
NAJERA, C
SANSANO, JM
YUS, M
EZQUERRA, J
YRURETAGOYENA, B
GRACIA, I
[J]. TETRAHEDRON, 1995, 51 (37) : 10259 - 10280
[2] CAREY FA, 2001, ADV ORG CHEM, P457
[3] Clayden J., 2002, TETR ORG CH, V23, P1
[4] Asymmetric synthesis of α,α-dibranched amines by the trimethylaluminum-mediated 1,2-addition of organolithiums to tert-butanesulfinyl ketimines
Cogan, DA
Ellman, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) : 268 - 269
[5] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines
Ellman, JA
Owens, TD
Tang, TP
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) : 984 - 995
[6] Stereoselective synthesis of 1,2-disubstituted β-amino alcohols by nucleophilic addition to N-tert-butanesulfinyl α-alkoxyaldimines
Evans, JW
Ellman, JA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) : 9948 - 9957
[7] Synthesis and structure-affinity relationships of 1,3,5-alkylsubstituted cyclohexylamines binding at NMDA receptor PCP site
Jirgensons, A
Kauss, V
Kalvinsh, I
Gold, MR
Danysz, W
Parsons, CG
Quack, G
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (06) : 555 - 565
[8] KATRITZKY AR, 1989, SYNTHESIS-STUTTGART, P66
[9] PAI KPP, 2002, TETRAHEDRON-ASYMMETR, V13, P2241
[10] AN EFFICIENT SYNTHESIS OF 1-PHENYL-1-PIPERIDINO-TRANS-4-METHYLCYCLOHEXANE - UNANTICIPATED TOTAL STEREOSELECTIVITY IN THE CATALYTIC-HYDROGENATION OF AN OLEFIN
VINICK, FJ
NOWAKOWSKA, J
JUNG, S
[J]. TETRAHEDRON LETTERS, 1987, 28 (07) : 741 - 744

← 1 →