Dual enantioselective control in asymmetric synthesis

Accounts of Chemical Research

Volumn 34, Issue 12, 2001, Pages 955-962

  Yong Hae Kim, ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ACRYLAMIDE DERIVATIVE; ALCOHOL DERIVATIVE; ALDEHYDE; AMIDE; AMINO ACID; CARBOXYLIC ACID DERIVATIVE; INDOLINE 2 CARBOXYLIC ACID; KETONE DERIVATIVE; LIGAND; TARTARIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; HYDROGENATION; MOLECULAR INTERACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0035667895     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar000187z     Document Type: Article

References (76)

1. Asymmetric reductions XIII, optically active benzyl-α-d alcohol and n-butyl-l-d alcohol via reduction by actively fermenting yeast
2. A reversal in stereoselectivity depending upon the age of a chiral lithium alkoxyaluminohydride reducing reagent
3. Asymmetric reduction with chiral reagents from lithium aluminum hydride and (+)-(2S,3R)-4-dimethylamino-3-methyl-l,2-diphenyl-2-butanol
4. Chiral oxazolinylferrocene-phosphine hybrid ligand for the asymmetric hydrosilylation of ketones
5. Iridium(I)-catalyzed asymmetric hydrogenation of prochiral imines; protic amines as catalyst improvers
6. Highly enantioselective synthesis of enantiomeric 2,3-dihydroxy thioester by using similar type of chiral sources derived from L-proline
7. 8BINOL: Asymmetric oxidation of sulfide to sulfoxide
8. 2-symmetric and symmetry induction
9. Asymmetric catalysis with heterobimetallic compounds
10. Chiral titanium complexes for enantioselective addition of nucleophiles to carbonyl groups
11. Asymmetric glyoxylate-ene reaction catalyzed by chiral titanium complexes: A practical access to α-hydroxy esters on high enantiomeric purities
12. Influence of external ligands and auxiliaries on the reactivity of low-valent titanium in McMurry reaction: Selectivity and mechanistic profile
13. Samarium dibromide, an efficient reagent for the pinacol coupling reactions
14. Ligand modified catalysts for the McMurry pinacol reaction
15. Stereoselective pinacol coupling in aqueous media
16. Pinacol coupling of aromatic aldehydes catalysed by a titanocene
17. New reagents for the old pinacol coupling reaction
18. Stereoselective pinacol coupling of 2,3-O-isopropylidene-D-glyceraldehyde
19. 6]. Synthesis of syn,syn-3-[N(alkoxycarbonyl)aminol 1,2- diols
20. 2-symmetrical HIV-protease inhibitors
21. Catalytic asymmetric dihydroxylation
22. Catalytic asymmetric dihydroxylation of tetrasubstituted olefins
23. Osmium catalyzed vicinal dihydroxylation of olefins by tert-butyl hydroperoxide under alkaline conditions
24. Sequencing reactions with samarium(II) iodide
25. Diverse methods for medium ring synthesis
26. New sequential reactions with single-electron-donating agents
27. 2, the kagan reagent
28. Efficient formation of pinacols from aldehydes or ketones mediated by samarium diiodide
29. Samarium iodide catalyzed pinacol coupling of carbonyl compounds
30. 2-Ti(O-iPr)4-MeOH systems
31. Enantiomerically pure cyclic trans-1,2-diols, diamines, and amino alcohols by intramolecular pinacol coupling of planar chiral mono Cr(CO)3 complexes of biaryls
32. From axial chirality to central chiralities: Pinacol cyclization of 2,2′-biaryldicarbaldehyde to trans-9,10-dihydrophenanthrene-9,10-diol
33. Samarium diiodide mediated synthesis of D-3,4,5,6-tetra-O-benzylmyoinositol
34. Mechanism of electrochemical pinacolization. The first asymmetric synthesis in a chiral medium
35. Partial asymmetric synthesis via a cyclic alkoxyphosphorane
36. 2: Synthesis of enantiomerically pure R and S quarternary tartaric acids
37. Samarium diiodide/hexamethylphosphoramide promoted dimerization of benzaldehydes
38. Intramolecular reductive cyclization of unsaturated keto- or aldo-esters by samarium(II) diiodide: A ready synthesis of bicyclic γ-lactones
39. Synthesis of substituted cyclooctanols by a samarium(II) iodide promoted 8-endo radical cyclization process
40. Studies of C-substituted tartaric acid. I. The preparation of optically active 2-methyltartaric and 2,3-dimethyltartaric acid
41. Stereocontrolled catalytic asymmetric reduction of α-ketoamides with oxazaborolidine derivatives from new chiral amino alcohols
42. Asymmetric 1,3-dipolar cycloaddition of nitrite oxides to new chiral acrytamides derived from (S)-indoline-2-carboxylic acid
43. Diastereoselective addition of organolithium to new chiral hydrazones
44. Asymmetric diels-alder and ene reactions in organic synthesis
45. Asymmetric diels-alder cycloaddition reactions with chiral α,β-unsaturated nacyloxazolidinones
46. 2AICI complexes of an N-acyloxazolidinone: NMR investigation
47. Chiral toluene-2, α-sultam auxiliaries: Asymmetric diels-alder reactions of N-enoyl derivatives
48. The preparation of optically active Δ2-isooxazolines. A model for asymmetric induction in the non-Lewis acid-catalyzed reactions at oppolzer's chiral sultam
49. Concerning the mechanism of the asymmetric Diels-Alder reaction: First crystal structure analysis of a Lewis acid complex of a chiral dienophile
50. Toward the development of a general chiral auxiliary. 1. Preparation of a new class of camphor lactam imides and their application to the construction of quaternary centers via Diels-Alder cycloaddition
51. A Lewis acid dependent asymmetric Diels-Alder process in the cyclization of new chiral acrylamides with dienes
52. The absolute configuration of some simple norbornane derivatives. A test of the conformational asymmetry model
53. 2-Norbornanediazonium ions revisited
54. Reduction of C=O
55. Topics in Current Chemistry
56. Asymmetric synthesis using chirally modified borohydrides. Part 3. Enantioselective reduction of ketones and oxime ethers with reagents prepared from borane and chiral amino alcohols
57. Asymmetric synthesis using chirally modified borohydrides. Part 4. Enanatioselective reduction of ketones and oxime ethers with the reagents prepared from borane and polymer-supported (S)-(-)-2-amino-3-(ρ-hydroxyphenyl)-1,1-diphenylpropan-l-ol
58. Highly enantioselective borane reduction of ketones catalyzed by chiral oxazaborolidines. Mechanism and synthetic implications
59. A stable and easily prepared catalyst for the enantioselective reduction of ketones. Applications to multistep syntheses
60. An efficient and catalytically enantioselective route to (S)-(-)-phenyloxirane
61. Asymmetric borane reduction of ketones catalyzed by oxazaborolidine
62. Enantioselective catalytic borane reductions of achiral ketones: Syntheses and application of two chiral β-amino alcohols from (S)-2-indoline carboxylic acid
63. Enantioselective reductions of ketones with oxazaborolidines derived from (R) and (S)-α,α-diphenyl-2-piperidine methanol
64. Enantiocontrolled reduction of prochiral aromatic ketones with borane using diastereoisomeric secondary aminoalcohols as chiral catalysts
65. Stereocontrolled enantioselective addition of diethylzinc to aldehydes using new chiral aminoalcohols
66. Quantum chemical modeling of chiral catalysis on the mechanism of catalytic enantioselective reduction of carbonyl compounds by chiral oxazaborolidines
67. Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes
68. Enantioselective addition of dialkylzincs to aldehydes promoted by chiral amino alcohol. Mechnism and nonlinear effect
69. Catalytic asymmetric induction. Highly enantioselective addition of dialkylzincs to aldehydes. Using chiral pyrrolidinylmethanols and their metal salts
70. Polymer-bound ephedrine as an efficient chiral catalyst for the enantioselective addition of dialkylzincs addition of dialkylzincs to aldehydes
71. Polyfunctional, structurally defined catalysts for the enantioselective addition of dialkylzinc reagents to aldehydes