Rhodium-catalyzed intramolecular reductive aldol-type cyclization: Application for the synthesis of a chiral necic acid lactone

• Motoyuki Isoda,
• Kazuyuki Sato,
• Kenta Kameda,
• Kana Wakabayashi,
• Ryota Sato,
• Hideki Minami,
• Yukiko Karuo,
• Atsushi Tarui,
• Kentaro Kawai and
• Masaaki Omote

Beilstein J. Org. Chem. 2022, 18, 1642–1648, doi:10.3762/bjoc.18.176

• to the literature, a Sharpless dihydroxylation of benzyl tiglate (8) to form a chiral diol 9 was followed by a Parikh–Doering oxidation to give the corresponding product 10 in 62% yield (Scheme 4) [58][59]. Subsequent acryloylation in the presence of DMAP and hydroquinone gave the intramolecular

Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups

• Xiaoyun Hu,
• Jianxin Guo,
• Cui Wang,
• Rui Zhang and
• Victor Borovkov

Beilstein J. Org. Chem. 2020, 16, 1875–1880, doi:10.3762/bjoc.16.155

• BINOL, 2,2-dimethyltetraphenyl-1,3-dioxolane-4,5-dimethanol (TADDOL) was also widely used as a C2 chiral diol. However, TADDOL-derived phosphoric acids were not comprehensively investigated as catalysts in Biginelli and Biginelli-like reactions yet. The first example of their successful application was

Recent applications of chiral calixarenes in asymmetric catalysis

• Mustafa Durmaz,
• Erkan Halay and
• Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

• to the noncovalent interactions, aluminum complexes of calixarene diphosphites 118a–e were synthesized via lower-rim functionalization of the p-tert-butylcalix[4]arene core with axially chiral diol ligands 117 (Scheme 37). The asymmetric MPV reduction of various substituted acetophenones were

Synthesis of a sucrose dimer with enone tether; a study on its functionalization

• Zbigniew Pakulski,
• Norbert Gajda,
• Magdalena Jawiczuk,
• Jadwiga Frelek,
• Piotr Cmoch and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2014, 10, 1246–1254, doi:10.3762/bjoc.10.124

• mixed with a chiral diol ligand forms complexes active in ECD in which a transfer of ligand chirality to the in situ-formed complex occurs in solution. Thus, stereochemistry of vic-diols can be easily assigned based on the helicity rule developed for this class of compounds. This rule correlates the

Enantioselective total synthesis of (R)-(−)-complanine

• Krystal A. D. Kamanos and
• Jonathan M. Withey

Beilstein J. Org. Chem. 2012, 8, 1695–1699, doi:10.3762/bjoc.8.192

• with sodium borohydride. Subsequent copper-mediated N–O bond cleavage gave chiral diol 8 in 97% ee (determined by HPLC analysis using a chiral stationary phase). Diol 8 had identical spectroscopic properties compared to those reported by Nakamura and Uemura and intercepted their synthesis of (R

Directed ortho,ortho'-dimetalation of hydrobenzoin: Rapid access to hydrobenzoin derivatives useful for asymmetric synthesis

• Inhee Cho,
• Labros Meimetis,
• Lee Belding,
• Michael J. Katz,
• Travis Dudding and
• Robert Britton

Beilstein J. Org. Chem. 2011, 7, 1315–1322, doi:10.3762/bjoc.7.154

• groups. The optimization and scope of this reaction are discussed, and the utility of this process is demonstrated in the one-pot preparation of a number of chiral diols as well as a short synthesis of the chiral ligand Vivol. Keywords: chiral diol; directed ortho-metalation; hydrobenzoin; Introduction

• provide a detailed account of this work as well as the application of these methods to a short synthesis of the chiral diol Vivol (4). Results and Discussion As indicated in Scheme 1, the optimized conditions for the directed ortho,ortho'-dimetalation of (R,R)-hydrobenzoin (3) involve the treatment of a

Diastereoselective and enantioselective reduction of tetralin- 1,4-dione

• E. Peter Kündig and
• Alvaro Enriquez-Garcia

Beilstein J. Org. Chem. 2008, 4, No. 37, doi:10.3762/bjoc.4.37

• access to this C2 symmetric chiral diol. Compound (−)-(1R,4R)-7 was previously obtained by HPLC separation of a 1 : 1 mixture of the cis- and trans-diols obtained in 55% yield from a four step sequence from (R)-1-tetralol [12]. Mono-reduction of 2 Mono-reduction was achieved with a reduced amount of

An exceptional P-H phosphonite: Biphenyl- 2,2'-bisfenchylchlorophosphite and derived ligands (BIFOPs) in enantioselective copper- catalyzed 1,4-additions

• T. Kop-Weiershausen,
• J. Lex,
• J.-M. Neudörfl and
• B. Goldfuss

Beilstein J. Org. Chem. 2005, 1, No. 6, doi:10.1186/1860-5397-1-6

• , FAA, Scheme 4) are crucial for the "bite" of the chiral diol unit and are constrained between 30° and 46° (Table 2), similar to fenchyl aryl angles previously analyzed in lithium fencholates. [54][55] In BIFOL, the asymmetry of the H-bond gives rise to two different fenchyl aryl angles (25° and 31