Journal ArticleDOI
Enantio- and diastereoselective aldol reactions of achiral ethyl and methyl ketones with aldehydes: the use of enol diisopinocampheylborinates
Ian Paterson,Jonathan M. Goodman,M. Anne Lister,Russell C. Schumann,Cynthia K. McClure,Roger David Norcross +5 more
TLDR
In this article, enol diisopinocampheylborinates, derived from achiral ethyl and methyl ketones by enolisation in the presence of tertiary amine bases (iPr2NEt or Et3N), undergo enantio-and diastereoselective aldol reactions with aldehydes.About:
This article is published in Tetrahedron.The article was published on 1990-01-01. It has received 214 citations till now. The article focuses on the topics: Aldol condensation & Aldol reaction.read more
Citations
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Journal ArticleDOI
Diastereoselection in lewis-Acid-mediated aldol additions.
TL;DR: The evolution of stereoselective Lewis-acid-mediated aldol-type addition up to the recent development of chiral Lewis acids is covered, which gives the main advantages in the Mukaiyama approach are the chemoselectivity of the reaction and the possibility of stereOSElective execution.
Journal ArticleDOI
Total Synthesis of Bryostatin 2
David A. Evans,Percy H. Carter,Erick M. Carreira,André B. Charette,Joëlle Prunet,Mark Lautens +5 more
TL;DR: The total synthesis of the marine macrolide bryostatin 2 is described in this paper, which relies on aldol and directed reduction steps in order to construct the anti-1,3-diol array present in each of the principal subunits (A, B, and C).
Journal ArticleDOI
Apparent Catalytic Generation of Chiral Metal Enolates: Enantioselective Dienolate Additions to Aldehydes Mediated by Tol-BINAP·Cu(II) Fluoride Complexes
Journal ArticleDOI
Aldolase Antibodies of Remarkable Scope
Torsten Hoffmann,Guofu Zhong,Benjamin List,Doron Shabat,James Anderson,Svetlana Gramatikova,Richard A. Lerner,Carlos F. Barbas +7 more
TL;DR: This paper describes the substrate specificity, synthetic scope, and efficiency of aldolase catalytic antibodies 38C2 and 33F12, which use the enamine mechanism common to the natural Class I a Aldolase enzymes.
Journal ArticleDOI
A practical synthesis of (+)-discodermolide and analogues: fragment union by complex aldol reactions.
TL;DR: In this paper, a practical stereocontrolled synthesis of (+)-discodermolide (1) has been completed in 10.3% overall yield (23 steps longest linear sequence).
References
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Enantioselective aldol condensations. 2. Erythro-selective chiral aldol condensations via boron enolates
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Double Asymmetric Synthesis and a New Strategy for Stereochemical Control in Organic Synthesis
TL;DR: In this article, it is shown that double asymmetric induction can be analyzed in terms of the single asymmetric reactions of each of the two chiral reactants, and a new strategy based on this rule for the predictable creation of new chiral centers is discussed and the use of this strategy for the synthesis of sugars and macrolides is presented.
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Chiral synthesis via organoboranes. 6. Asymmetric allylboration via chiral allyldialkylboranes. Synthesis of homoallylic alcohols with exceptionally high enantiomeric excess
TL;DR: The effect of changes in the chiral ligand on boron has also been studied in this article, showing that wide variations in the structure of the allylic moiety can be accommodated.
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Practical enantioselective Diels-Alder and aldol reactions using a new chiral controller system
TL;DR: In this paper, le complexe cyclique Al [−N(SO 2 CF 3 )(CHPh) 2 (CF 3 SO 2 )N-] R, R=i-Bu, CH 3
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Enantiomeric Z- and E-crotyldiisopinocampheylboranes. Synthesis in high optical purity of all four possible stereoisomers of .beta.-methylhomoallyl alcohols
Herbert C. Brown,Krishna S. Bhat +1 more
TL;DR: Synthese des 4 stereoisomeres du methyl-3 pentene-4 ol-2 par reaction de (butene-2 diisopinocamphenyl) borane avec l'acetaldehyde as mentioned in this paper.