Programmed Synthesis of a Contiguous Stereotriad Motif by Triple Stereospecific Reagent-Controlled Homologation

被引：29

作者：

Sun, Xun ^{[1
]}

Blakemore, Paul R. ^{[1
]}

机构：

[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 17期

基金：

美国国家科学基金会;

关键词：

BORONIC ESTERS; STEREOCONTROLLED SYNTHESIS; CHIRAL CARBENOIDS; CHEMISTRY;

D O I：

10.1021/ol402049y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

All distinct diastereoisomers of a contiguous stereotriad motif were separately targeted by a triple chain extension of B-phenethyl boronic esters using four unique presentation sequences of enantiomorphs of 1-[H-2]-1-chloro-2-(1,3-dioxolan-2-yl)ethyllithium. The (R)- or (S)-configured chloroalkyllithium reagents were generated by sulfoxide lithium exchange from the appropriate scalemic p-tolyl chloroalkyl sulfoxides using phenyllithium (THF, -78 degrees C). Stereotriad synthesis was accomplished in a single reaction vessel [7-19% yield, typical dr >= 74 (target):26 (Sigma all other isomers)] and implemented by a simple algorithm consisting of reagent charging and temperature cycling events.

引用

页码：4500 / 4503

页数：4

共 36 条

[21] Reagent-controlled stereoselective synthesis of (±)-gallo- and (±)-epigallo-catechin gallates
Tanaka, Hiroshi
Chino, Ayaka
Takahashi, Takashi
TETRAHEDRON LETTERS, 2012, 53 (20) : 2493 - 2495
[22] A Reagent-Controlled SN2-Glycosylation for the Direct Synthesis of β-Linked 2-Deoxy-Sugars
Issa, John Paul
Bennett, Clay S.
SYNTHESIS-STUTTGART, 2014, 46 (15): : A106 - A107
[23] Reagent-controlled SN2-glycosylation for the direct synthesis of β-linked 2-deoxy-sugars
Issa, John P.
Bennett, Clay S.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[24] A Reagent-Controlled SN2-Glycosylation for the Direct Synthesis of β-Linked 2-Deoxy-Sugars
Issa, John Paul
Bennett, Clay S.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (15) : 5740 - 5744
[25] Fully reagent-controlled asymmetric synthesis of (-)-spongidepsin via the Zr-catalyzed asymmetric carboalumination of alkenes (ZACA reaction)
Zhu, Gangguo
Negishi, Ei-ichi
ORGANIC LETTERS, 2007, 9 (15) : 2771 - 2774
[26] Metallated S,O-acetals from stereodefined dithioorthoformate monooxides: Potential oxygen bearing chiral carbenoids for stereospecific reagent controlled homologation (StReCH)
Barsamian, Adam L.
Blakemore, Paul R.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
[27] Divergent Total Synthesis of the Tricyclic Marine Alkaloids Lepadiformine, Fasicularin, and Isomers of Polycitorols by Reagent-Controlled Diastereoselective Reductive Amination
In, Jinkyung
Lee, Seokwoo
Kwon, Yongseok
Kim, Sanghee
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) : 17433 - 17442
[28] Transition-Metal-Free Reduction of -Keto Thioesters with Hydrosilanes at Room Temperature: Divergent Synthesis through Reagent-Controlled Chemoselectivities
Maity, Rajib
Das, Bhanuranjan
Das, Indrajit
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (10) : 2347 - 2353
[29] Hg(II) reagent-controlled stereoselective synthesis of 2,5-cis- and 2,5-trans-polyhydroxylated pyrrolidines
Chikkanna, D
Han, HS
SYNLETT, 2004, (13) : 2311 - 2314
[30] Reagent-Controlled Divergent Synthesis of 2-Amino-1,3-Benzoxazines and 2-Amino-1,3-Benzothiazines
Putta, V. P. Rama Kishore
Vodnala, Nagaraju
Gujjarappa, Raghuram
Tyagi, Ujjawal
Garg, Aakriti
Gupta, Sreya
Pujar, Prasad Pralhad
Malakar, Chandi C.
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (02): : 380 - 396

← 1 2 3 4 →