Sparteine-mediated asymmetric nucleophilic substitution at prochiral, sp3-hybridized carbon

被引：11

作者：

Muller, P ^{[1
]}

Nury, P ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 4, Switzerland

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 18期

关键词：

D O I：

10.1021/ol0062749

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Phenyl-1,3-dioxolanes (1) react with organolithium reagents (2), associated with (-)-sparteine, in the presence of BF3. OEt2 to afford chiral monosubstitution products 3, Enantioselectivity is highest if both 1 and 2 carry alkyl substituents in the ortho position. However, the enantioselectivity decreases in the case of very bulky substituents such as tert-butyl or phenyl.

引用

页码：2845 / 2847

页数：3

共 50 条

[1] A new family of sp3-hybridized carbon phases
徐宁
李建福
黄勃龙
王保林
Chinese Physics B, 2016, (01) : 716 - 720
[2] Asymmetric Syntheses of 3,4-Disubstituted Tetrahydroquinoline Derivatives Using (+)-Sparteine-mediated Electrophilic Substitution
Choi, Yun Soo
Kang, Kyoung Hee
Park, Yong Sun
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (05) : 1500 - 1503
[3] A new family of sp3-hybridized carbon phases
Xu, Ning
Li, Jian-Fu
Huang, Bo-Long
Wang, Bao-Lin
CHINESE PHYSICS B, 2016, 25 (01)
[4] sp3-Hybridized carbon atoms are the building blocks
Nesper, R.
Vogel, K.
Bloechl, P.E.
Angewandte Chemie (International Edition in English), 1993, 32 (05):
[5] Polymorphic Phases of sp3-Hybridized Carbon under Cold Compression
Zhou, Rulong
Zeng, Xiao Cheng
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (17) : 7530 - 7538
[6] (+)-Sparteine-Mediated Substitution of o-Benzyl-N-pivaloylaniline with Ketones
Ko, Yi Kyung
Im, Chan
Do, Junghwan
Park, Yong Sun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (16) : 3460 - 3467
[7] Carbon-Based Leaving Group in Substitution Reactions: Functionalization of sp3-Hybridized Quaternary and Tertiary Benzylic Carbon Centers
Mahoney, Stuart J.
Lou, Tiantong
Bondarenko, Ganna
Fillion, Eric
ORGANIC LETTERS, 2012, 14 (13) : 3474 - 3477
[8] sp3-Hybridized superhard trigonal carbon allotropes: A first principle study
Kou, Junru
Zhou, Yalan
Luo, Peng
Gan, Li-Hua
COMPUTATIONAL MATERIALS SCIENCE, 2021, 190
[9] Effect of sp3-hybridized defects on the oscillatory behavior of carbon nanotube oscillators
Guo, Taiyu
Ding, Tony Weixi
Pei, Qing-Xiang
Zhang, Yong-Wei
PHYSICS LETTERS A, 2011, 375 (24) : 2400 - 2404
[10] METHYLCYCLOBUTYL CATION - SIMPLE SP3-HYBRIDIZED CARBOCATION
KIRCHEN, RP
SORENSEN, TS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (20) : 6687 - 6693

← 1 2 3 4 5 →