Fluorescence-Based Screening of Asymmetric Acylation Catalysts through Parallel Enantiomer Analysis. Identification of a Catalyst for Tertiary Alcohol Resolution

2001 ◽  
Vol 66 (16) ◽  
pp. 5522-5527 ◽  
Author(s):  
Elizabeth R. Jarvo ◽  
Catherine A. Evans ◽  
Gregory T. Copeland ◽  
Scott J. Miller
Keyword(s):  
Tertiary Alcohol ◽  
Enantiomer Analysis

ChemInform Abstract: Fluorescence-Based Screening of Asymmetric Acylation Catalysts Through Parallel Enantiomer Analysis. Identification of a Catalyst for Tertiary Alcohol Resolution.

ChemInform ◽  
2010 ◽  
Vol 32 (47) ◽  
pp. no-no
Author(s):  
Elizabeth R. Jarvo ◽  
Catherine A. Evans ◽  
Gregory T. Copeland ◽  
Scott J. Miller
Keyword(s):  
Tertiary Alcohol ◽  
Enantiomer Analysis

The synthesis of norbornanes with functionalized carbon substituents at a bridgehead. 1-(3-Oxonorborn-1-yl)ethanone and 1-(3-oxonorborn-1-yl)-2-propanone

1992 ◽  
Vol 70 (5) ◽  
pp. 1492-1505 ◽  
Author(s):  
Peter Yates ◽  
Magdy Kaldas
Keyword(s):  
Acetic Acid ◽  
Carboxylic Acid ◽  
Hydrogen Bromide ◽  
Tertiary Alcohol ◽  
Ethyl Bromoacetate ◽  
Second Molar ◽  
Molar Equivalent ◽  
Acid Lactone ◽  
Basic Hydrolysis ◽  
Hydrolysis Of

Treatment of 2-norobornene-1-carboxylic acid (7) with one equivalent of methyllithium in ether followed by a second molar equivalent after dilution with tetrahydrofuran gave 1-(norborn-2-en-lyl)ethanone (10) and only a trace of the tertiary alcohol 11. Reaction of 7 with formic acid followed by hydrolysis gave a 4:3 mixture of exo-3- and exo-2-hydroxynorbornane-1-carboxylic acid (16 and 17), whereas oxymercuration–demercuration gave only the exo-3-hydroxy isomer 16. Oxidation of 16 and 17 gave 3- and 2-oxonorbornane-1-carboxylic acid (27 and 29), respectively. Oxymercuration–demercuration of 10 gave exclusively 1-(exo-3-hydroxynorborn-1-yl)ethanone (30), which was also prepared by treatment of 16 with methyllithium in analogous fashion to that used for the conversion of 7 to 10. Oxidation of 30 gave 1-(3-oxonorborn-1-yl)ethanone (1). Dehydrobromination of exo-2-bromonorbornane-1-acetic acid and dehydration of 2-hydroxy-norbornane-2-acetic acid derivatives gave 1-(norborn-2-ylidene) acetic acid derivatives to the exclusion of norborn-2-ene-1 -acetic acid derivatives. Treatment of exo-5-acetyloxy-2-norobornanone (52) with ethyl bromoacetate and zinc gave ethyl exo-5-acetyloxy-2-hydroxynorbornane-(exo- and endo-2-acetate (53 and 54). Reaction of 53 with hydrogen bromide gave initially ethyl endo-3-acetyloxy-exo-6-bromonorbornane-1-acetate (59), which was subsequently converted to a mixture of 59 and its exo-3-acetyloxy epimer 61. Catalytic hydrogenation of this mixture gave a mixture of ethyl endo- and exo-3-acetyloxynorbornane-1 -acetate (62 and 63). Basic hydrolysis of this gave a mixture of the corresponding hydroxy acids, 70 and 71; the former was slowly converted to the latter at pH 5. Oxidation of the mixture of 70 and 71 gave 3-oxonorbornane-1-acetic acid (72). Treatment of the mixture with methyllithium as for 16 gave a mixture of 1-(endo- and exo-3-hydroxynorborn-1-yl)-2-propanone (73 and 74), which was oxidized to 1-(3-oxo-norborn-1-yl)-2-propanone (2). Reaction of exo-2-hydroxynorbornane-1-acetic acid lactone (75) with methyllithium in ether gave (1-(exo-2-hydroxynorborn-1-yl)-2-propanone (76), which on oxidation gave the 2-oxo isomer 78 of 2.

Enzymatic resolution of oxalate esters of a tertiary alcohol using porcine pancreatic lipase

1993 ◽  
pp. 1093 ◽  
Author(s):  
Ian Brackenridge ◽  
Raymond McCague ◽  
Stanley M. Roberts ◽  
Nicholas J. Turner
Keyword(s):  
Pancreatic Lipase ◽  
Tertiary Alcohol ◽  
Porcine Pancreatic Lipase ◽  
Enzymatic Resolution

Catalytic enantioselective organozinc addition toward optically active tertiary alcohol synthesis

2008 ◽  
Vol 8 (3) ◽  
pp. 143-155 ◽  
Author(s):  
Manabu Hatano ◽  
Kazuaki Ishihara
Keyword(s):  
Optically Active ◽  
Tertiary Alcohol ◽  
Alcohol Synthesis

ChemInform Abstract: Pseudo-C3-Symmetric Tertiary Alcohol Building Block via Group-Selective Hydroalumination: A Synthesis of (-)-Malyngolide.

ChemInform ◽  
2010 ◽  
Vol 32 (38) ◽  
pp. no-no
Author(s):  
Takao Suzuki ◽  
Ken Ohmori ◽  
Keisuke Suzuki
Keyword(s):  
Building Block ◽  
Tertiary Alcohol

RESOLUTION OF AN ALIPHATIC TERTIARY ALCOHOL

1948 ◽  
Vol 70 (11) ◽  
pp. 3966-3966 ◽  
Author(s):  
William von E. Doering ◽  
Harold H. Zeiss
Keyword(s):  
Tertiary Alcohol

HIV-1 Protease Inhibitors with a Transition-State Mimic Comprising a Tertiary Alcohol: Improved Antiviral Activity in Cells

2010 ◽  
Vol 53 (2) ◽  
pp. 607-615 ◽  
Author(s):  
A.K. Mahalingam ◽  
Linda Axelsson ◽  
Jenny K. Ekegren ◽  
Johan Wannberg ◽  
Jacob Kihlström ◽  
...  
Keyword(s):  
Antiviral Activity ◽  
Transition State ◽  
Protease Inhibitors ◽  
Tertiary Alcohol ◽  
Hiv 1 ◽  
In Cells

ChemInform Abstract: Catalytic Enantioselective Organozinc Addition Toward Optically Active Tertiary Alcohol Synthesis

ChemInform ◽  
2009 ◽  
Vol 40 (27) ◽  
Author(s):  
Manabu Hatano ◽  
Kazuaki Ishihara
Keyword(s):  
Optically Active ◽  
Tertiary Alcohol ◽  
Alcohol Synthesis

Stereochemical control of tertiary alcohol: aldol condensation of lactate derivatives

2001 ◽  
Vol 42 (31) ◽  
pp. 5249-5252 ◽  
Author(s):  
Tomoyuki Kamino ◽  
Yoshihisa Murata ◽  
Nobuyuki Kawai ◽  
Seijiro Hosokawa ◽  
Susumu Kobayashi
Keyword(s):  
Aldol Condensation ◽  
Tertiary Alcohol ◽  
Stereochemical Control
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