Dual Stereoselectivity in the Dialkylzinc Reaction Using (−)-β-Pinene Derived Amino Alcohol Chiral Auxiliaries

2009 ◽  
Vol 74 (6) ◽  
pp. 2337-2343 ◽  
Author(s):  
Caitlin M. Binder ◽  
April Bautista ◽  
Marek Zaidlewicz ◽  
Marek P. Krzemiński ◽  
Allen Oliver ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Chiral Auxiliaries

ChemInform Abstract: A Simple and Convenient Synthesis of β-Amino Alcohol Chiral Auxiliaries Based on Limonene Oxide.

ChemInform ◽  
2001 ◽  
Vol 32 (48) ◽  
pp. no-no
Author(s):  
Will Chrisman ◽  
Jason N. Camara ◽  
Kim Marcellini ◽  
Bakthan Singaram ◽  
Christian T. Goralski ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Chiral Auxiliaries ◽  
Convenient Synthesis ◽  
Limonene Oxide

A simple and convenient synthesis of β-amino alcohol chiral auxiliaries based on limonene oxide

2001 ◽  
Vol 42 (34) ◽  
pp. 5805-5807 ◽  
Author(s):  
Will Chrisman ◽  
Jason N Camara ◽  
Kim Marcellini ◽  
Bakthan Singaram ◽  
Christian T Goralski ◽  
...  
Keyword(s):  
Amino Alcohol ◽  
Chiral Auxiliaries ◽  
Convenient Synthesis ◽  
Limonene Oxide

Synthesis of Axially Chiral 2,2’-Bisphosphobiarenes via a Nickel-Catalyzed Asymmetric Ullmann Coupling: General Access to Privileged Chiral Ligands without Optical Resolution

2020 ◽  
Author(s):  
Ziqing Zuo ◽  
Raphael Kim ◽  
Donald Watson
Keyword(s):  
Optical Resolution ◽  
Chiral Ligands ◽  
Chiral Auxiliaries ◽  
Axially Chiral ◽  
Ullmann Coupling

<div><p>We report an asymmetric Ullmann-type homocoupling of <i>ortho-</i>(iodo)arylphosphine oxides and <i>ortho</i>-(iodo)arylphosphonates that results in highly enantioenriched axially chiral bisphosphine oxides and bisphosphonates in good yields and excellent enantioselectivities. These products are readily converted to enantioenriched biaryl bisphosphines without need for chiral auxiliaries or optical resolution. This process provides a straightforward and practical route for the development of previously uninvestigated atroposelective biaryl bisphosphine ligands.</p></div>

Synthesis and Reactivity of Precolibactin 886

2019 ◽  
Author(s):  
Seth Herzon ◽  
Alan R. Healy ◽  
kevin wernke ◽  
Chung Sub Kim ◽  
Nicholas Lees ◽  
...  
Keyword(s):  
Colorectal Cancer ◽  
Gene Cluster ◽  
Amino Alcohol ◽  
Biomimetic Synthesis ◽  
Cross Linking ◽  
E Coli ◽  
Hplc Purification ◽  
Structural Assignment ◽  
Biosynthetic Precursor ◽  
Double Oxidation

<div>The clb gene cluster encodes the biosynthesis of metabolites known as precolibactins and colibactins. The clb pathway is found in gut commensal E. coli, and clb metabolites are thought to initiate colorectal cancer via DNA cross-linking. Precolibactin 886 (1) is one of the most complex isolated clb metabolites; it contains a 15-atom macrocycle and an unusual 5-hydroxy-3-oxazoline ring. Here we report confirmation of the structural assignment via a biomimetic synthesis of precolibactin 886 (1) proceeding through the amino alcohol 9. Double oxidation of 9 afforded the unstable α-ketoimine 2 which underwent macrocyclization to precolibactin 886 (1) upon HPLC purification (3% from 9). Studies of the putative precolibactin 886 (1) biosynthetic precursor 2, the model α-ketoimine 25, and the α-dicarbonyl 26 revealed that these compounds are susceptible to nucleophilic rupture of the C36–C37 bond. Moreover, cleavage of 2 produces other known clb metabolites or biosynthetic intermediates. This unexpected reactivity explains the difficulties in isolating full clb metabolites and accounts for the structure of a recently identified colibactin–adenine adduct. The colibactin peptidase ClbP deacylates synthetic precolibactin 886 (1) to form a non-genotoxic pyridone, suggesting precolibactin 886 (1) lies off-path of the major biosynthetic route.</div>

A Short, Affordable, One-Pot Synthesis of a Camphor-Derived Amino Alcohol

1995 ◽  
Vol 25 (19) ◽  
pp. 2975-2980 ◽  
Author(s):  
Robert M. Przeslawski ◽  
Suzanne Newman ◽  
Edward R. Thornton ◽  
Madeleine M. Joullié
Keyword(s):  
Amino Alcohol ◽  
One Pot ◽  
One Pot Synthesis
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