Enantioselective Horner-Wadsworth-Emmons reaction using chiral lithium 2-aminoalkoxides

被引：0

作者：

Kumamoto, T ^{[1
]}

Koga, K ^{[1
]}

机构：

[1] UNIV TOKYO, FAC PHARMACEUT SCI, BUNKYO KU, TOKYO 113, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1997年 / 45卷 / 04期

关键词：

chiral base; chiral lithium 2-aminoalkoxide; Horner-Wadsworth-Emmons reaction; enantioselective asymmetric synthesis; chiral axis;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Chiral lithium 2-aminoalkoxides ((1R,2S)-4) were applied as chiral bases for the enantioselective Horner-Wadsworth-Emmons reaction between achiral phosphonates (2) and 4-tert-butylcyclohexanone (1). A chiral olefin ((R)-3b) was obtained in up to 52% enantiomeric excess (ee). It is shown that the formation of the lithium aldolate intermediate is reversible and is not responsible for the asymmetric induction.

引用

页码：753 / 755

页数：3

共 50 条

[41] Quantum mechanical investigation of the Horner-Wadsworth-Emmons reaction of benzyl pyridyl ketone
Kim, Jinyoung
Park, Kwang-Su
Yeo, Woon-Seok
Chong, Youhoon
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2008, 29 (06) : 1269 - 1272
[42] ASYMMETRIC HORNER-WADSWORTH-EMMONS REACTIONS USING MESO DIALDEHYDES AS SUBSTRATES
KANN, N
REIN, T
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15): : 3802 - 3804
[43] Poly(phosphonate)-mediated Horner-Wadsworth-Emmons reactions
Steinbach, Tobias
Wahlen, Christian
Wurm, Frederik R.
POLYMER CHEMISTRY, 2015, 6 (07) : 1192 - 1202
[44] Improved Horner-Wadsworth-Emmons olefination of aldehydes.
Petroski, RJ
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U67 - U67
[45] A facile method for the stereoselective Horner-Wadsworth-Emmons reaction of aryl alkyl ketones
Sano, S
Yokoyama, K
Shiro, M
Nagao, Y
CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (05) : 706 - 709
[46] Electronic effects on the Z(cis)-selectivity of Horner-Wadsworth-Emmons olefination reaction
Reddy, AM
Gopal, VR
Rao, VJ
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1996, 35 (04): : 312 - 317
[47] Diastereoselective Horner-Wadsworth-Emmons reaction for the synthesis of tetrasubstituted alkenes with an axis of chirality
Sano, Shigeki
Abe, Shinobu
Azetsu, Tomohiro
Nakao, Michiyasu
Shiro, Motoo
Nagao, Yoshimitsu
LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (11) : 798 - 801
[48] Highly Z-selective synthesis of α,β-unsaturated nitriles using the Horner-Wadsworth-Emmons reaction
Ando, Kaori
Okumura, Miho
Nagaya, Shigeo
TETRAHEDRON LETTERS, 2013, 54 (15) : 2026 - 2028
[49] Intramolecular Horner-Wadsworth-Emmons Olefination Route to Annulated Carbohydrates
Synlett, 1 (24):
[50] Use of lithium hexafluoroisopropoxide as a mild base for Horner-Wadsworth-Emmons olefination of epimerizable aldehydes
Blasdel, LK
Myers, AG
ORGANIC LETTERS, 2005, 7 (19) : 4281 - 4283

← 1 2 3 4 5 →