Asymmetric synthesis of axially chiral 1-(2′-methyl-3′-indenyl)naphthalenes via prototropic rearrangements of stable rotamers of 1-(2′-methyl-1′-indenyl)naphthalenes

被引：10

作者：

Baker, RW ^{[1
]}

Reek, JNH ^{[1
]}

Wallace, BJ ^{[1
]}

机构：

[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(98)01369-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of methyl (R)-1-(p-tolylsulfinyl)naphthalene-2-carboxylate 2 with 2-methylindenyllithium affords the -ac rotamer of methyl (S)-1-(2'-methyl-1'-indenyl)naphthalene-2-carboxylate 6 in 63% ee. Heating -ac-6 at 80 degrees C leads to the formation of an 18:1 mixture of -ac:+sc-6 rotamers, with a barrier to atropisomerisation of Delta G double dagger(353) = 28.4 kcal mol(-1) (+sc to -ac). Prototropic rearrangements of the rotamers of 1-(2'-methyl-1'-indenyl)naphthalenes to 1-(2'-methyl-3'-indenyl)naphthalenes occur with retention of the axial stereogenic element. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6573 / 6576

页数：4

共 8 条

[1]

Baker RW, 1997, CHEM COMMUN, P506

[2] Central to axial chirality transfer via double bond migration: Asymmetric synthesis and determination of the absolute configuration of axially chiral 1-(3'-indenyl)naphthalenes [J].