scholarly journals Erratum: Corrigendum: Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines

Nature ◽  
2013 ◽  
Vol 503 (7475) ◽  
pp. 300-300 ◽  
Author(s):  
Sergey V. Pronin ◽  
Christopher A. Reiher ◽  
Ryan A. Shenvi
Keyword(s):  
Tertiary Alcohols ◽  
Tertiary Alkyl

The Thermal Decomposition of Alkoxycarbonyl Thiocyanates and Isothiocyanates

1975 ◽  
Vol 53 (6) ◽  
pp. 907-912 ◽  
Author(s):  
Dennis Liotta ◽  
Robert Engel
Keyword(s):  
Thermal Decomposition ◽  
Primary Alcohols ◽  
Reduced Pressure ◽  
Tertiary Alcohols ◽  
Alkyl Amines ◽  
Tertiary Alkyl

Alkoxycarbonyl thiocyanates and isothiocyanates have been decomposed thermally under reduced pressure at temperatures of 240–375°. Primary systems yield primarily alkyl thiocyanates, whereas secondary and tertiary systems yield alkyl isothiocyanates. The viability of using this reaction in a conversion of primary alcohols to primary alkyl thiols and secondary and tertiary alcohols to tertiary alkyl amines is discussed.

Zn-Mediated Hydrodeoxygenation of Tertiary Alkyl Oxalates

Synlett ◽  
2020 ◽  
Author(s):  
Hegui Gong ◽  
Yang Ye ◽  
Guobin Ma ◽  
Ken Yao
Keyword(s):  
Functional Groups ◽  
Reduction Method ◽  
Structural Motifs ◽  
Tertiary Alcohols ◽  
Tertiary Alkyl

AbstractHerein we describe a general, mild, and scalable method for hydrodeoxygenation of readily accessible tertiary alkyl oxalates by Zn/silane under Ni-catalyzed conditions. The reduction method is suitable for an array of structural motifs derived from tertiary alcohols that bear diverse functional groups, including the synthesis of a key intermediate en route to estrone.

Reactions of Tertiary Hypohalites

1971 ◽  
Vol 49 (16) ◽  
pp. 2664-2671 ◽  
Author(s):  
V. Boido ◽  
O. E. Edwards
Keyword(s):  
Silver Oxide ◽  
Short Chain ◽  
Metallic Silver ◽  
Mercuric Oxide ◽  
Tertiary Alcohols ◽  
Convenient Synthesis ◽  
Homolytic Decomposition ◽  
Tertiary Alkyl

Metallic silver initiates short-chain homolytic decomposition of tertiary alkyl hypochlorites and hypobromites. Evidence is presented that the reaction of tertiary alcohols with silver oxide – mercuric oxide – bromine involves formation and homolytic decomposition of alkyl hypobromite followed by cyclization of γ-bromo alcohols. A convenient synthesis of tricyclo[4.3.1.03,8]decan-4-one (4-proto-adamantanone) is described.

Stereoinversion of tertiary alcohols to tertiary-alkyl isonitriles and amines

Nature ◽  
2013 ◽  
Vol 501 (7466) ◽  
pp. 195-199 ◽  
Author(s):  
Sergey V. Pronin ◽  
Christopher A. Reiher ◽  
Ryan A. Shenvi
Keyword(s):  
Tertiary Alcohols ◽  
Tertiary Alkyl

scholarly journals Tertiary alcohol preferred: Hydroxylation oftrans-3-methyl-L-proline with proline hydroxylases

2011 ◽  
Vol 7 ◽  
pp. 1643-1647 ◽  
Author(s):  
Christian Klein ◽  
Wolfgang Hüttel
Keyword(s):  
Relative Yield ◽  
Heme Iron ◽  
Tertiary Alcohol ◽  
Type Ii ◽  
Tertiary Alcohols ◽  
P450 Monooxygenases ◽  
Non Heme Iron ◽  
Sterically Hindered ◽  
Tertiary Alkyl ◽  
Proline Hydroxylase

The enzymatic synthesis of tertiary alcohols by the stereospecific oxidation of tertiary alkyl centers is a most-straightforward but challenging approach, since these positions are sterically hindered. In contrast to P450-monooxygenases, there is little known about the potential of non-heme iron(II) oxygenases to catalyze such reactions. We have studied the hydroxylation oftrans-3-methyl-L-proline with the α-ketoglutarate (α-KG) dependent oxygenases,cis-3-proline hydroxylase type II andcis-4-proline hydroxylase (cis-P3H_II andcis-P4H). Withcis-P3H_II, the tertiary alcohol product (3R)-3-hydroxy-3-methyl-L-proline was obtained exclusively but in reduced yield (~7%) compared to the native substrate L-proline. Forcis-P4H, a complete shift in regioselectivity from C-4 to C-3 was observed so that the same product as withcis-P3H_II was obtained. Moreover, the yields were at least as good as in control reactions with L-proline (~110% relative yield). This result demonstrates a remarkable potential of non-heme iron(II) oxygenases to oxidize substrates selectively at sterically hindered positions.

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