Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/14898
Title: Asymmetric ligand transformation reactions
Authors: PULLARKAT APPUKUTTAN SUMOD
Keywords: Chiral auxiliary; Diels-Alder reactions; Asymmetric synthesis; Chiral diphosphines, Terminal alkenols, Hydrophosphination.
Issue Date: 17-Oct-2005
Source: PULLARKAT APPUKUTTAN SUMOD (2005-10-17). Asymmetric ligand transformation reactions. ScholarBank@NUS Repository.
Abstract: The organopalladium complex containing ortho-metalated (R)-(1-(dimethylamino)ethyl)naphthalene as the chiral auxiliary has been used to promote the asymmetric [4+2] Diels-Alder reaction between the cyclic dienes, 3,4-dimethyl-1-phenylphosphole and 3,4-dimethyl-1-phenylphosphole-1-sulfide with sulfonated and non-sulfonated phosphine and arsine functionalized dienophiles viz., diphenylvinylphosphine sulfide, divinylphenylphosphine sulfide, divinylphenylphosphine, diphenylvinylarsine and divinylphenylarsine. The platinum analogue of the complex was also employed to promote the asymmetric Diels-Alder reaction between 3,4-dimethyl-1-phenylphosphole and phosphine functionalized terminal alkenols, 3-diphenylphosphanyl-but-3-en-1-ol and 2-diphenylphosphanyl-prop-2-en-1-ol, culminating in the synthesis of P-chiral phosphanorbornene systems with hydroxyl functionality. The chiral templates were also utilized for hydrophosphination of the aforementioned alkenols thereby yielding diphosphines with chirality residing on the carbon backbone.
URI: http://scholarbank.nus.edu.sg/handle/10635/14898
Appears in Collections:Ph.D Theses (Open)

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