An efficient enantioselective synthesis of a set of (R)-phenylalkylesters and their analogues amides via enzymatic acylation of 1-phenylethanol (rac-1) and 1-phenylethanamine (rac-2) using carboxylic acids with different chain-lengths as green acyl donor is reported. Three lipases are used: Candida antarctica B immobilized on acrylic resin (CAL-B) and two free lipases: Pseudomonas cepacia (PCL) and Candida rugosa (CRL). The CAL-B shows an excellent selectivity during the acylation of rac-1 without restriction due to the acyl carbon chain-length, the (R)-esters (1 a-1 f) were obtained enantiopures (ee up to 99 %). For the first time, the PCL catalyzed O-acylation allows smoothly to (R)-(1 d-1 f) with high selectivity (E⋙200) is described. The conversions increase with the length of the carbon-chain of the acyl donor (28.7 % � C � 40 %). The CRL shows less selective and provided the (R) (1 b-1 e) with 77 % � ee p � 86.4 %. Due to its high thermostability, the CAL-B is used for the N-acylation of rac-2 and provides access to enantioenriched (R)-fatty amides (2 d-2 f) (60.7 % � ee p � 74.4 %) and the remained (S)-2 with ee s > 91 %.