Condensation Oligomers with Sequence Control but without Coupling Reagents and Protecting Groups via Asymmetric Hydroformylation and Hydroacyloxylation

被引：18

作者：

Foarta, Floriana ^{[1
]}

Landis, Clark R. ^{[1
]}

机构：

[1] Univ Wisconsin Madison, Dept Chem, 1101 Univ Ave, Madison, WI 53706 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 22期

关键词：

HIGHLY ENANTIOSELECTIVE HYDROFORMYLATION; SOLID-PHASE SYNTHESIS; CARBOXYLIC-ACIDS; ANTI-MARKOVNIKOV; (+)-PATULOLIDE C; TERMINAL ALKYNES; OLEFINS; ESTERS; POLYMERIZATION; COPOLYMERS;

D O I：

10.1021/acs.joc.6b02210

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel strategy, free of coupling reagents and protection/deprotection steps, for the synthesis of oligo(2-hydroxyacid)s containing up to four monomer units with atom economy, sequence specificity, and control of stereocenter configuration is described. The strategy comprises an iterative application of the sequence asymmetric hydroformylation/ oxidation/alkyne hydroacyloxylation that features catalytic, atom-economical C-C and C-O bond forming reactions. Asymmetric hydroformylation with Rh-bisdiazaphospholane catalyst introduces each stereocenter with high enantio- (ca. 93% e.e.), diastereo- (up to 25:1 d.r.), and regioselectivity (>50:1) at low catalyst loadings and mild pressures. The side chain in each monomer is tailored by choosing from a variety of readily available alkynes.

引用

页码：11250 / 11255

页数：6

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