The challenge of implementing and executing a legal contract in a machine has been gaining significant interest recently with the advent of blockchain, smart contracts, LegalTech and IoT technologies. Popular software engineering methods, including agile ones, are unsuitable for such outcome-critical software. Instead, formal specifications are crucial for implementing smart contracts to ensure they capture the intentions of stakeholders, also that their execution is compliant with the terms and conditions of the original natural-language legal contract. This thesis concerns supporting the semi-automatic generation of formal specifications of legal contracts written in Natural Language (NL). The main contribution is a framework, named Contratto, where the transformation process from NL to a formal specification is subdivided into 5 steps: (1) identification of ambiguous terms in the contract and manual disambiguation; (2) structural and semantic annotation of the legal contract; (3) discovery of relationships among the concepts identified in step (2); (4) formalization of the terms used in the NL text into a domain model; (5) generation of formal expressions that describe what should be implemented by programmers in a smart contract. A systematic literature review on the main topic of the thesis was performed to support the definition of the framework. Requirements were derived from standard business contracts for a preliminary implementation of tools that support the transformation process, particularly concerning step (2). A prototype environment was proposed to semi-automate the transformation process although significant manual intervention is required. The preliminary evaluation confirms that the annotation tool can perform the annotation as well as human annotators, albeit novice ones.